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10.1.1.1.3.2.1.1 From Alkyl (2-Acylphenoxy)acetates

DOI: 10.1055/sos-SD-110-00529

Kwiecień, H.Science of Synthesis Knowledge Updates, (20144189.

The cyclization of methyl or ethyl (2-acylphenoxy)acetates 349 (obtained from 2-hydroxybenzaldehydes or ketones and alkyl haloacetates) carried out in the presence of bases such as sodium methoxide, magnesium methoxide, potassium carbonate, and potassium hydroxide leads to alkyl benzo[b]furan-2-carboxylates 350 (Scheme 157).[‌291‌‌296‌]

Meeeee 888 Meee-Meeeeeeee Meeeeeeeeee ee Meeee (8-Meeeeeeeeee)eeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌]

Meeeeeeeeee 888

M8 M8 M8 M8 M8 M8 Meeeeeeeee Meeee (%) ee 888 eeee 888 Mee
M M MMe M M Me Me(MMe)8, MeMM 88 [‌888‌]
M M MMe M M Me MeMMe, MeMM 88 [‌888‌]
MM M M M Me Me MeMMe, MeMM 88 [‌888‌]
M M M M Me Me MeMMe, eeeeeee 88 [‌888‌]
M Me MMe M M Me Me(MMe)8, MeMM 88 [‌888‌]
M MM8 M MMe M Me MMM, MeMM 88 [‌888‌]

Meee eeeeeee eeeeeeee eeeeeeeee ee ee eeeeeeeeeeee eeeee eeeeeee, eeeee eee ee eee eeeee eeeeeee; eeeeeee, ee eeeeeee eeeeeeeee eeeeeeeeeee eeeeeee e eeeee[e]eeeee-8-eeeeee­eeeee. Mee eeeeeee, eeeeee [8-(eeeeeeeee)-8-eeeeeeeeeeeee]eeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = MMe; M8 = Me), eeeeeeee ee eeeeeeee ee 8-(eeeeeeeee)-8-eeeeeeeeeeeeeeeeeee eeee eeeeee eeeeeeeeeeee, eeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee eeeeeeee ee eeeeee 8-(eeeeeeeee)eeeee[e]eeeee-8-eeeeeeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = MMe; M8 = Me) ee 88% eeeee,[‌888‌] eee eeee eeeeee eeeeeeeee, eee eeeee ee eeee 88%.[‌888‌] Meeeeeeee ee eeeee (8-eeeeee-8-eeeeeeeeeeeeee)eeeeeee (888, M8 = MM; M8 = M8 = M8 = M; M8 = Me; M8 = Me) eeee eeeeee eeeeeeee ee eeeeeee eeeee eeeee 8-eeeeeee-8-eeeeeeeeeee[e]eeeee-8-eeeeeeeeeee (888, M8 = MM; M8 = M8 = M8 = M; M8 = Me; M8 = Me) ee 88% eeeee.[‌888‌] Meeee 8-eeeee-8-eeeeeeeeeeee[e]eeeee-8-eeeeeeeeeee (888, M8 = M8 = M8 = M; M8 = Me; M8 = MMe; M8 = Me) eee ee eeeeeeee ee eeeeeeeeeee ee eeeee (8-eeeee-8-eeeeee-8-eeeeeeeeeeeeee)eeeeeee (888, M8 = M8 = M8 = M; M8 = Me; M8 = MMe; M8 = Me) ee eee eeeeeeee ee eeeeee eeeeeeee ee eeeeeee,[‌888‌] eeeeeee eeeee (8-eeee-8-eeeeeeeeeeee)eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeeee 8,8-eeeeeee eeeeeee eeeeeeeeeeeeee eeeee eeeeeeeeeee ee eeeeeee eeeee 8-eeeee-8-eeeeeee-8-eeeee-8,8-eeeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee ee e eeeeeee ee M8/M8 eee- eee eeeee-eeeeeeeeeeeee.[‌888‌] Mee eeeeeeee eeeeee eeee eeeeeeeee ee eee eeeeeeeee ee eee eeee eeeee: eeeeee, eeeeeeeee, ee eeeeeeeeee eeeeee eeee ee eee eeeeeeeee ee eeeeeeee ee eeeee eee 8-eeeeeeeeeeeeee eeeee eee 8-eeeeeee eeeeee eee eee, eeeeeee eeeeeeee ee 8-eeeeee eeeeeeeeeee eeeee eee eeee eeeeeeeeee eeeee e eeeeee eeeeeeeee eeeeeee ee eee- eee eeeee-eeeeeeeeeeeee.[‌888‌] Mee eeeeeeeeee eeeeeeee ee eee 8,8-eeeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee eeee eeeeeeeee eeeeeeeee ee eeeeeeeee 8,8-eeeeeee eeeee ee eeeeeeeeeee, eeeeee eee eeeeeeeeeeeee eeeee[e]eeeee-8-eeeeeeeeeeee.[‌888‌]

Meeeeeeeeeeeee eeeee eeeeeeeeeee ee eeeee (8-eeeeee-8-eeeeeee-8-eeeeeeeeeeee)eeeeeee (888, M8 = M8 = M8 = M; M8 = MM8; M8 = MMe; M8 = Me) eeeeeeee ee eeeeeeeeeee eee eeee ee eeeeeeee ee eee eeee eeee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee ee eeeeeeeee eeeeeee ee eeee eeeeeeee eeeee 8-eeeeeee-8-eeeeeeeeee[e]eeeee-8-eeeeeeeeeee (888, M8 = M8 = M8 = M; M8 = MM8; M8 = MMe; M8 = Me), eeeee ee ee eeeeeeeeeeee eee eee eeeee eeeeeeeee ee eeee-(+)-eeeeeeeeeeeeee, ee eeeeeeee ee eee eeeeee eeeeeeeee eeeeeee eeeeeee eeeeeeeeeee MM.[‌888‌] Mee eeeee (8-eeeeee-8-eeeeeee-8-eeeeeeeeeeee)eeeeeee (888, M8 = M8 = M8 = M; M8 = MM8; M8 = MMe; M8 = Me) eeeeee eee eee eeeeeeeee eee ee eeeeeeee ee 88% eeeee ee eeeeeeeeee ee eeeeeeeeeeee eeeeeeeee 8-eeeeeee-8-eeeeeee-8-eeeeeeeeeeeeeeeee eeee eeeee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeee.[‌888‌]

Meee-eeeeeeeee eeeeeeeeeee ee eeeee-eeeeee eeeeeeeeeeeeeeeeeee ee e eeeeeeeee eeeee ee eeeeeeeeeeeee. Meeeeeeee ee eeeeeeeeeeeee eeeee-eeeeee eeeeeeeeeeeeeeeeeee 888 eee 888 (Meeeee 888) eeee eeeeeeeee eeeeeeeee ee 8,8-eeeeeee ee 88 °M eeeeeeee eeeeeeeeeeee eeeee 888 eee 888, eeeeeeeeeeee. Meeeeeeeeeeee ee eee eeeee eeee eeeeeee eeeeeeeeeeee eeee eeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeeeeeee ee eeeeeee 8-eeeeeeeeeeeee[8,8-e]eeeee (888) eee 8-eeeeeeeeeeeee[8,8-e]eeeee (888), eeeeeeeeeeee.[‌888‌] Meeee ee eee eeeeeee eeee eee eeeeeeeeeeeee eee-eeeeee ee eeeeeeeeeeeeee eeeeee eeee eee eeee-eeeeeeeee eeeeeeeeeee ee eeeee (8-eeeeeeeeeee)eeeeeeee,[‌888‌] eee eee eeee eeee eeee eee eeeeeee eeee ee δ 8.8 eee (MMMM8M) ee eeeeeeee ee eeeee 8M MMM eeeeeee,[‌888‌] ee eee ee eeeeeee eeee eee eeeeeeeeee ee eeeee 888 eee 888 eeee eeeeeeee eee eeeeeee eeeeee eee ee eee eeeee eeee.

Mee eeeeeeee eeeeeeeeeeeeeeeeeee 888 eee 888 eee ee eeeeeeee ee eeee eeeeee ee eeeeeeee ee eeeee-eeeeeee eeeeeeeee eeee eeeee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeee.

Meeeee 888 Meeeeeeee ee Meeeeeeeeeeee Meeeeee[8,8-e]- eee Meeeeee[8,8-e]eeeeee eee Meeeeeeeeee ee eeeee-Meeeee Meeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee 8-(Meeeeeeee)eeeee[e]eeeee-8-eeeeeeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = MMe; M8 = Me):[‌888‌]

Meeeee eeeeeeeeeeee (88 e, 888 eeee) eee eeeee ee e eeeeeee ee 8-(eeeeeeeee)-8-eeeeeeeeeeeeeeeeeee (88 e, 888 eeee) eee M8MM8 (88 e, 888 eeee) ee eeeeeee (888 eM) eeee eeeeeeee eee eee eeeeeee eee eeeeee ee eeeeee eee 8 e. Meee ee eee eeeeeee eee eeeeeeeee eee eee eeeeee M8M eee eeeee. Mee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee [MeMM ee eeeeeee (MMMMMMM: eeeeeeeeee)] ee eeeeee eeeeee [8-(eeeeeeeee)-8-eeeeeeeeeeeee]eeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = MMe; M8 = Me) ee eeee eeeeee eeeeeee; eeeee: 88 e (88%); ee 888 °M.

Meeeee [8-(eeeeeeeee)-8-eeeeeeeeeeeee]eeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = MMe; M8 = Me; 88 e, 88.8 eeee) eee eeeee ee e eeee ee MeMMe ee MeMM (eeee 8.8 e. ee Me eee 888 eM ee eeeee MeMM) eee eeeeeee eeeeee eeee eeee ee eeeeeee eeeee eeeeee. Meeee 88 eee, eee eeee eee eeeeee eee eee eeeeeee eeeeeeeeeeee; eeeee: 8.8 e (88%); ee 888 °M (MeMM).

Meeee 8-Meeeeeeeeee[e]eeeee-8-eeeeeeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = Me; M8 = Me):[‌888‌]

M eeeeeee ee eeeee (8-eeeeeeeeeeeee)eeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = Me; M8 = Me; 88.88 e, 88 eeee), MeMMe (8.88 e, 88 eeee), eee eeeeeee (88 eM) eee eeeeee ee eeeeee eee 8.8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeeeee eeeeeee M8M eee MMMe8. Mee eeeeeee eeeee eee eeeee eee eeeeeeeeeeee ee eeee eee eeeeeee; eeeee: 8.8 e (88.8%); ee 88–88 °M.

Meeee 8-Meeeeee-8-eeeeeeeeee[e]eeeee-8-eeeeeeeeeee (888, M8 = M8 = M8 = M; M8 = MM8; M8 = MMe; M8 = Me):[‌888‌]

Me e eeeeeee eeeeeeee eeee ee 8-eeeeeee-8-eeeeeee-8-eeeeeeeeeeeeeeeee (888 e, 8.888 eee) ee eeeee MeMM (8.8 M) eee eeeee eeeeeeee MMM (88%, 88.8 e, 8.888 eee) eee eee eeeeeee eee eeeeee ee eeeeee eee 88 eee. MeMM eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeeee eeeee eeeeeee eee eeeeeeeee ee MMM (8.8 M). Mee eeeeeeeeee eee eeeeee ee 8 °M eee eeeee eeeeeeeeeeee (888 eM, 8.888 eee) eee eeeee. Mee eeeeeee eee eeeeee ee ee eee eeeeeee eee 88 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeee eeee M8M (8 M) eee eeeeeeeee eeee MeMMe (8 × 8 M). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8 M) eee eeeee (8 M), eeeee (Me8MM8), eee eeeeeeeeeeee ee eeee eeeee (8-eeeeee-8-eeeeeee-8-eeeeeeeeeeee)eeeeeee (888, M8 = M8 = M8 = M; M8 = MM8; M8 = MMe; M8 = Me) ee e eee eeeee; eeeee: 888.8 e (88%); ee 888–888 °M.

MMM (88 eM, 8.888 eee) eee eeeee ee e eeee ee eeeee (8-eeeeee-8-eeeeeee-8-eeeee­eeeeeee)eeeeeee (888, M8 = M8 = M8 = M; M8 = MM8; M8 = MMe; M8 = Me; 888.8 e, 8.888 eee) ee MeMM (8.8 M) eee eee eeee eee eeeeee ee eeeeee eee 8 e. Mee eeeeeee eee eeeeee ee ee eee eee eeeeeeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee eeee MeMM (888 eM), eee eeeee eeeee eeeeeee eeeeeeee ee 88 °M ee eeeeeee eee eeeeeee ee e eeeeee eeeee; eeeee: 88.8 e (88%); ee 888–888 °M.

8-Meeeeeeeeeeee[8,8-e]eeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeee eeeeeeeeeeee (8.88 e, 8.88 eeee) ee eeeeeee (88 eM) eee eeeee ee e eeeeeee ee 8-eeeeeee-8-eeeeeeee (8.88 e, 8.88 eeee) eee M8MM8 (8.88 e, 88.8 eeee) ee eeeeeee (888 eM) eee eeeeee ee eeeeee eee 8 e eeeee M8. Mee M8MM8 eee eeeeeeee eee eee eee eeeeeeee eee eeeeeeeeeeee. M8M eee eeeee ee eee eeeeeee eee eee eeeeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeee eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeee eeeee 8-(8-eeeeeeeeeeeeeeeee-8-eeeee)eeeeeee (888); eeeee: 8.8 e (88%); ee 88–88 °M.

Meeee 8-(8-eeeeeeeeeeeeeeeee-8-eeeee)eeeeeee (888; 8.888 e, 8.88 eeee) eee eeeee ee e eeeeeeee eeeee eeeeeeeeee MMM (8.888 e, 8.88 eeee) ee 8,8-eeeeeee (88 eM) eee eee eeeeeeeee eeeeeee eee eeeeeee ee 88 °M eee 8 e eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeeee ee M8M (88 eM) eee eee eeee eee eeeeeeeee eeee ee MMe, eeeeeee eee 8 e ee 88 °M, eee eeeeeeeee eeee Me8M. Mee eeeeeee eee eeeee eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8); eeeee: 8.888 e (88%); ee 888–888 °M.

References