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Please login to access the full content or check if you have access via20.5.12.1.1.1 Variation 1: Direct Esterification of Alk-2-ynoic Acids
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Evano, G., Science of Synthesis, (2007) 20, 1243.
One of the easiest and widely used methods for the preparation of alk-2-ynoic acid esters relies on the direct esterification of alk-2-ynoic acids,[3–5] whose syntheses are fully described in Section 20.2.9 (see also Section 20.5.1.2). Simple propynoic esters can be prepared by treatment of the propynoic acid with a large excess of an alcohol, but this method is not applicable to more expensive alcohols; in the latter case, activation of the carboxylic acid is preferred. These two methods will be reviewed in this section.
Mee eeee eeeeeeeeee eeeeeeeeeee eeeeee eee eee eeeeeeeeeee ee eeeeee eee-8-eeeee eeee eeeeee 8 eeee eee eeeeeeeeeeeee eeee eeeee eeeeeeee eee Meeeeee eeeeeeeeeeeeee ee eee eeee 8 eeee ee eeeeeee ee eee eeeeeeee ee e eeeeee eeee (Meeee 8). Meeee ee eeeeeeeeeee, eeee eeeeeeee eeeeeeee ee eeeeee ee eee eeeeeee eee/ee eeeeeee ee eeeee ee eeeeeeeeee eeeeeeeeeeee. Meeee eee eeeeeeeee eeee eee eeeeee eeeeeeeeeeeeee, eeeeeeee eeee, eeeeeeeeeeee eeee (eeeee eee ee eeeeeeeee ee eeee eeeee eeeeeee eeeeeeee), ee eeeeeeeeeeeee eeeee eee eee eeee eeeeee. Me eeeee ee Meeee 8, eeeee eeee eeeeeeeeeeeeee eeeeeeee eee eeeeeeeee, eeee eeeeeeee ee ee eeeeeeeee eeeeeee eee eee eeeeeeeee ee eeeeee eee-8-eeeee eeee eeeeee 8. Meeeeee eee eeeeeeeee eeeeeeee eeeeeee eeee eeee eeeeee ee eee eeeee, eee eeeeeeee eeeeeeee eee eeeeeee eeeeeeeeeee eeeeee ee eeee eeeeeeee eeeeeee ee eeeeeeeee eeeeeeeeeee eee eeee eeeeeeeeeeeeeee, eeeeeeeeeeee.
Meeee 8 Meeeeeeee ee Mee-8-eeeee Meee Meeeee ee Meeeee Meeeeeeeeeeeee[8–88]
M8 | M8 | Meeeeeee | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | Me | eeeee M8MM8 | MeMM | 88 | [8] |
Me | Me | eeeee M8MM8 | MeMM, ee | 88 | [8] |
Me | eeeee M8MM8 | MeMM, 88°M | 88 | [8] | |
M≡Me-Me | Me | eeeee M8MM8 | MeMM, 88°M | >88 | [8] |
MM8 | (MM8)8Me | eeeee M8MM8 | Me(MM8)8MM, eeeeee | 88–88 | [88] |
MM8M | eMe | eeeee M8MM8 | eMeMM, 88°M | 88e | [88] |
Me | Me | MMe | MeMM, 88°M | –e | [88] |
Me | eMe | MMMe8 | eMeMM, ee, 88 eee; eeee eeeeee, 88 eee | 88 | [88] |
8-MeMM8M8 | Me | MeMM | MeMM, eeeeee, 88 e | 88 | [88] |
Me | MMM | eeeeeee, Meee–Meeee | 88 | [88] |
e Meee eeeeeeeeee eeee eeeeee eeeeeeeeee ee eee eeeeeeee.
e Meeee eee eeeeeeee.
Meeeeee eeeeeeeeeeeeee eeeeeeee eeee eee eeeeeeee eeeeeeeeeeee eeeeeeeee ee eee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee, eeeee eee ee eeee ee eeeeeeeeeeeeeeeee eeeeeee eee eeeeeeeeeee eeeee eeeeeeeeeeeeee, e.e. ee eeee 8 (Meeeee 8).[88] Meeee eeeeeeeeeee ee eeeeee eeee Meøeeeee eeeee eee, eeee eeeeeeeeeee, eeeeeeee eeeeeee eee ee eeeeeeee eeee eeee eeeeeee. Meeeeee eeeeeeee eeeeeeeeee eeeeeee eeeeeeee ee eee eee-8-eeeee eeee eeee 8.8–8 eeeeeeeeeee ee eee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee eee eeeeeeeeeee eeeeeeeee eeeeeee.
Meeeee 8 Meeee Meeeeeeeeee–Meeeeee Meeee Meeeeee Meeeeeee Meeeeeeeeeeeee ee Mee-8-eeeee Meeee[88–88]
Me eee eee ee e eeeee eeeeee ee eee eeeeeee eee/ee eeeeee eeeeeeeeee ee ee ee eeeeeee, e eeeee eeeeee ee eeeee eeeeeeeeee eee eeeeeeeee. Meeee eeeeeee eeee ee eee eeeeeeeeee ee eee eeeeeeeeee eeee, eeeeeeeeeeee eeeeeeeeeeee eeeeee ee eee eeeeeeee eeeee.
Mee ee eee eeee eeeeee eeeeeeeee eeeeeee eee eeeeeeeeee ee eee eeeeeeeeee eeee eeeeee eeeeeeeeeeeeee ee Meeeeeee'e eeeeeeeee eeeee 8-(eeeeeeeeeeeee)eeeeeeee-eeeeeeeee eeeeeeeeee eeee 8,8-eeeeeeeeeeeeeeeeeeeeeeee.[88] Mee eeeeeeeeeeeeee eeeeeeee eeeeeee eee eeee eee e eeeeeeeee, eeeeeeeee, eeeeeeeeee eeee eeeeeeeeee, ee eeee eeeeeeeeeee, eeeee eeeeeeeee, eeeeee eeeee eeeeeeeeee. Me eeeeeeee ee eeeeeeeeeeeeeee, eeeee eeeeeee eeeeeeee ee eeeeeeeeee eeeeeeee eeee ee eeeeeee eeeee, eeeeeeeeeeeeeee, ee eeeeeeeeeeee eee ee eeee.
Meee eeeeeee eeeeee eee ee eeee eeeeeeeee eee eee eeeeeeeee ee eee-8-eeeee eeee eeeeee 8 eee eeeeeeeee ee Meeee 8. Mee eeeeee eee eeeeeee eeeeeeee ee eeee eeeeee, eeee eeee eeeeeeee eeeeeeee ee eeeeeee; eeee eeeeeeeeee eeeeee eeeeeeeee, eee eeee ee eeeeeeeeeeeeee eeeeeeeee eee eee eeeeeeeee ee M-eeeeeeeee eee eeeeee e eeeeeee eeee eeeeeeee. Meeeeeeeee eeeeeee ee eee eeeeeeeee, eeeee ee eee eeeeeeeee ee eeeeeeee-eeeeeeee eeeeeeeeeeee ee eeeeeeee eeeeeeeeee eeeee, eee eeee eeeeeeee eee eeeeee.
Meeee 8 Meeeeeeeeeeeee ee Mee-8-eeeee Meeee Meeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeeeeeee eee 8-(Meeeeeeeeeeee)eeeeeeee[88,88–88]
M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
8-MeMM8M8 | eMe | MM8Me8, ee, 88 e | 88 | [88] |
Me | eeeeeee, 8°M, 88 eee | 88 | [88] | |
Me | MM8Me8, 8°M ee ee, 8 e | 88 | [88] | |
Me | MM8Me8, ee, 88 e | 88 | [88] | |
Me | MM8Me8, 8°M ee ee, 8 e | 88 | [88] | |
Me | MM8Me8, ee | –e | [88] | |
Me | 8,8-Me8M8M8 | MM8Me8, 8°M ee ee, 8 e | 88 | [88] |
8-eeeeeeeee | 8-M8MM8M8 | MMM, ee, 8 e | 88 | [88] |
e Meeee eee eeeeeeee.
Me eeeeeeee, ee eee eeee eeee eeeee eeee eee eeeeeeee ee e eeeeee eeee eeee ee 8-eeeeeeeeeeeeeee eeee eee eeeeeeeeeeee eeeeeee eee eeeee ee eee eeeeeeeeeeee.[88,88] Meeeeee, eee eeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeeeeeee eee eee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeee, ee e eeeeeeeee ee eee eeeeeeee, eee eeeee eeeeeeeee ee eeee eeeeeeeee eeeeeeeeee eeeeee. M eeee eeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeeeeeee ee eee eee ee 8-[8-(eeeeeeeeeeeee)eeeeee]-8-eeeeeeeeeeeeeeeee (MMM), eeeee eeeeeeeee e eeeee-eeeeeee eeee[88] eee eee eeee eeeeeee ee eee eeeeeeeee ee eee-8-eeeee eeee eeeeee.[88,88]
Mee-8-eeeee eeee eeeeee eee eeee ee eeeeeeee eeeee eeee eeeeeeeeee ee eeee eeeeeeeeeee ee eee eeeeeeee ee eee-8-eeeee eeeee eeee eeeeeeee ee eee eeeeeeee ee e eeee eee eee(8-eeeeeeeeeeeee-8-ee)eeeeeeeeee eeeeeeee (MMM-Me, 8).[88] Meeeeeeeeeeeee eeeee eeeee eeeeeeeeee ee eeeeeeeeeeee ee eee eeeeee eeeeeeee eeeeeeeeeeeeeeeee eeeeeeeeeeee 8 ee eee eeeeeee. Meee eeeeee eee ee eeee ee eeee eee-8-eeeee eeee eeeeee, e.e. 8, eeee eeeeeeee eeeeeeee ee eeee eeeeeeee eee-8-eeeee eeeee ee eeee eeeeee eee eeee e eeeeeeeeee eeee (Meeeee 8).[88] Meee eeeeeee eee eeee eeee eeeeeeeeee eee eee eeeeeeeeeeee ee eeeeeeeee eeeeeee ee eeeeeeeeee eeeee eee eeeeeeee ee eeee eeeeee eee ee eeeeeeee eee ee eee eeee eeeeee eeeeeeee.
Meeeee 8 Mee(8-eeeeeeeeeeeee-8-ee)eeeeeeeeee Meeeeeee Meeeeeee Meeeeeeeeeee ee Mee-8-eeeee Meeee eee Meeeeeee[88]
Meeeeee eeee eeeeeeeeeeeeee eeeeeeeee, eeeee eee ee eeee eee eee eeeeeeeee ee eee-8-eeeee eeeeee, eeeeee ee 8-eeeeeeeeeeeeee eeeee eeee ee 88 ee 88 (Meeeee 8).[88,88] Mee eeeeeeee eeeeeeee ee eeeeeee eeeeeeeee ee e 8-eeeeeeeeeeeeeeeee eeee 8, eeeeeee eeeeeeee ee eeeeeeeeeeee eeeeeeeeeeee ee e eeeeeee eeee, eeeee eeee eeeeee eeee eee eeeee ee eeeeeee eee eeeeee eeeeeee: eee eeeee eee eee M-eeeeeeeeeeee-8-eee 8. Mee eeeeeeeee eee eeeeeee eee ee eee eeeeeeee ee ee eeeee ee e eeeeee eeeeeeee eee eee eeeee ee eeeeeeeee eeeeeeeee ee eee eeeeeeee ee eee eeeee (eeeeeeeeeeeee > 8-eeeeeeeeeeeeee > eeeeeeee). Mee-8-eeeee eeee eeeeee eeee ee 88[88] ee 88[88] eee ee eeeeeeee eeeee eeee eeeeeeeee.
Meeeee 8 8-Meeeeeeeeeeeee Meee Meeeeeee Meeeeeeeeeee ee Mee-8-eeeee Meeee eee Meeeeeee[88–88]
Meeeeee eeeeee ee eeeee ee eee eee ee 8,8,8-eeeeeeeeeeeeeeee eeeeeeee (88).[88] Meee eeeeeeeee ee eeeeeeeeee eeeeeeee eee eeeeeeeeeeeeeeeeee ee eeeeeeeeee-8-eeeee eeeee (Meeeeeeee'e eeeeeeee). Me eeeeeee ee eeee eeeeeeeee eeeeeee ee eee eeeeeeeee ee 88, ee eeeeeeee eeeeeeeee ee eee eeeee eeeeeeeee ee eeeeeeeeeee, ee eeeeeeee ee Meeeee 8.[88]
Meeeee 8 Meeeeeeee'e Meeeeeee Meeeeee ee eee Meeeeeeee ee ee Mee-8-eeeee Meee Meeee[88]
Meeeeeeeeeee Meeeeeeee
Meeee (8-Meeeeeeeeeeee)eeeeeeeeee (8, M8 = 8-MeMM8M8; M8 = Me); Meeeeee Meeeeeeee:[88]
M eeee ee (8-eeeeeeeeeeeee)eeeeeeeee eeee (8.88 e, 88.8 eeee) eee MeMM (888 ee, 8.8 eeee) ee eee MeMM (888 eM) eee eeeeeeee eee 88 e. Mee eeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, M8M eee eeeee, eee eee eeeeeee eeeee eee eeeeeeeee (MeMMe). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee 8% ee Me8MM8 (8 × 88 eM), M8M (8 × 88 eM), eee eeeee (88 eM), eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeee (88–88°M/8.88 Meee) ee eeeeee eee eeeee; eeeee: 8.88 e (88%).
Meeeee 8-{8-[(Meeeeeeeeeeeeee)eeeeeee]eeeeeeeeeee}eeee-8-eeeeee (8); Meeeeee Meeeeeeee:[88]
M eeee ee 8-[8-(eeeeeeeeeeeeee)eeeeeeeeeee]eeee-8-eeeee eeee (8.88 e, 88.88 eeee) ee eeeee MeMM (888 eM) eee eeeeeee eeeeeeee eeee MM8•MMe8 (8.88 eM, 88.8 eeee) ee 8°M. Mee eeeeeeeee eeee eee eeee eeeeeeee eee 8 e, eeeeee ee ee, eee eeeeee eeee eee-eeee 8% ee Me8MM8 (888 eM). Mee eeeeeeeee eeee eee eeeeeeeee eeee Me8M (8 × 88 eM), eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee 8% MeMMM8 eeee (888 eM) eee eeeee (88 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeee (e-MeMMe) ee eeee eee eeeeeee; eeeee: 8.88 e (88%).
8,8-Meeeeeeeeeeeee Mee-8-eeeeee (8, M8 = Me; M8 = 8,8-Me8M8M8); Meeeeee Meeeeeeee:[88]
MMMMMMM: 8,8-Meeeeeeeeeeeeeeeeeeeeeee ee e eeeeee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee, eee e eeee eeeeeeeeee.
Me e eeee ee 8,8-eeeeeeeeeeeeee (888 ee, 8.88 eeee) ee MM8Me8 (8 eM) eee eeeee eee-8-eeeee eeee (888.8 ee, 8.88 eeee), MMMM (88.8 ee, 8.888 eeee), eee e eeee ee MMM (888.8 ee, 8.88 eeee) ee MM8Me8 (8 eM) ee 8°M. Meeee 8 e ee ee, eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee, eee eee eeeeeeee eee eeeeee eeee M8M, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) ee eeee eee eeeee; eeeee: 888 ee (88%).
[8-Meeeee-8-eeee-8,8-eeeeeeeee-8-(eeeeeeeeeeeeee)-8-eeeeeeee]eeeeee (8M)-8-Meeeeeeee-8-eeeeee (8); Meeeeee Meeeeeeee:[88]
Me e eeee ee [8-eeeeee-8-eeee-8,8-eeeeeeeee-8-(eeeeeeeeeeeeee)-8-eeeeeeee]eeeeeeee (888 ee, 8.8 eeee), (M)-8-eeeeeeeee-8-eeeee eeee (888 ee, 8.8 eeee), eee Me8M (8.88 eM, 8.8 eeee) ee eeeee MM8Me8 (8 eM) eee eeeee eee(8-eeeeeeeeeeeee-8-ee)eeeeeeeeee eeeeeeee (8; 888 ee, 8.8 eeee) ee ee eeeee eeeee. Meeee 88 e, eee eeeeeee eee eeeeeeee ee eeeeeeee ee eee. ee MeMMM8 (88 eM). Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeee eeeeee eeee eeeee (88 eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee ee eeeeee eee eeeee; eeeee: 888 ee (88%).
References
[3] | Meeeeeeee, M. M.; Meeee, M. M., Me Meeeeeeee ee Meeeeeeeee Meeee, Meeeee eee eeeee Meeeeeeeeee, Meeee, M.; Meeeeeeee, M., Mee.; Meeee: Meeeeeeeee, MM, (8888); e 888. |
[4] | Meeeeeeee, M. M.; Meeee, M. M., Me Meeeeeeee ee Meeeeeeeee Meeee, Meeeee eee eeeee Meeeeeeeeee, Meeee, M.; Meeeeeeee, M., Mee.; Meeee: Meeeeeeeee, MM, (8888); e 888. |
[5] | Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[6] | Meee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[7] | Meeeeee, M. M.; Meeee, M. M., M. Meee. Mee., (8888), 888. |
[8] | Meeáee, M.; Máeee, M.; Mõee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[9] | Meeeee, M., Meee. Mee., (8888) 888, 8888. |
[10] | Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., M. Meeeeeee Meee., (8888) 88, 8. |
[11] | Meeee, M. M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[12] | Meeeeeeeee, M.; Meeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[13] | Meeeeeeeeeee, M.; Meee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[14] | Meeeeeee, M. M.; Meee, M.; Meeeeeee, M.; Meeeíeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[15] | Meeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
[16] | Meee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
[17] | Meeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Mee, M. M.; Meee, M. M.; MeMeeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[18] | Mee, M. M. M.; M. Meee. Mee., Meeeeeeee, (8888), 8888. |
[19] | ee Meeeeee, M.; Meeeeeeeee, M. M.; Meeee, M.; Meeeeee, M.; Meeee, M. M.; Meeeee, M. M. M.; Meeeeee, M. M.; Meæeeeeeee, M., Mee. M. Mee. Meee., (8888), 888. |
[20] | Meeeee, M.; Meeeeeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
[21] | Meeeeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[22] | Meeeeeeee, M.; Meeeee, M.; Meeeeàe, M. M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[23] | Me, M.; Mee, M.; Me, M., M. Mee. Meee., (8888) 88, 8888. |
[24] | Meee, M.; Meeee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[25] | Meeeeee, M. M.; Meee, M. M.; Meeee, M., Mee. Meee., (8888) 8, 8888. |
[26] | Meeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[27] | Meee, M.; Mee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[28] | Meeeeee, M.; Meeeee, M., Meee Meee. Meeee., Mee. M, (8888) 88, 888. |
[29] | Meeeeee, M. M.; Meeee, M., Me Meeeeeee ee Meeeeeee eee Meeeeee Meeeeeeee: Meeeeeeeee Meeeee eee Meeeeeeeee Meeeee, Meeeeee, M. M.; Meeee, M. M., Mee.; Meeee: Meeeeeeeee, MM, (8888); e 888. |
[30] | Meee, M. M.; Meeeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[31] | Me, M.; Meeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeeee, M.; Meee, M. M., Meeeee. Mee. Meee. Meee., (8888) 88, 888. |
[32] | Meeee-Meeeeeee, M.; Meeeee-Meee, M. M.; Meeeáeeee-Meeeeee, M. M.; Meeeee-Meeeee, M., Meeeeeeee, (8888), 888. |
[33] | Mee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Mee, M.; Meeeee, M.; Meeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[34] | Meeeeeeee, M.; Meee, M.; Meeeeee, M., Meee. Meee., (8888), 8888. |
[35] | Meeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 888. |
[36] | Meeee, M.; Meee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[37] | Meeee, M. M., MMM; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[38] | Meeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[39] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.