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10.13.1.4.2.1.1.5.3 Variation 3: Introduction of Hydroxyalkyl and Related Groups

DOI: 10.1055/sos-SD-010-00559

Joule, J. A.Science of Synthesis, (200110513.

Indoles react with aldehydes and ketones under acid catalysis: the initial products, indol-3-yl carbinols such as 705 cannot usually be isolated, for in the acidic conditions they dehydrate to produce 3-alkylidene-3H-indolium cations, e.g. 706, in Scheme 233 which shows the reaction of 2-methyl-1H-indole 704 with acetone under anhydrous conditions giving the simplest isolable salt 706 of this class.[‌726‌] As will be shown below, the usual situation is the isolation of a product of further reaction of the 3-alkylidene-3H-indolium cation as an electrophile with a second equivalent of the indole.

Meeeee 888 Meeeeeee ee 8-Meeeee-8M-eeeeee eeee Meeeeee ee Meee[‌888‌]

Meeeeeee ee eeeeeee eeee 8-(eeeeeeeeeeeee)eeeeeeeeeeee ee eee eeeeeeee ee eeee (eee Meeeeee eeeeeeee) eeeee eeeeeeeee eee eeeeee eeeeeee eeeeeee 888 eeeee eeee eee eeeee eee eeeee eeeee eeeeeeeee eeeeeeeeeeeeee eee eeeeeee (eee eeee eee eeeee eeeeee eeeeeeeeeeee eeeeeeee eeeee, eeee ee eeeeeeee) (Meeeee 888).

Meeeee 888 Meeeeeee ee eee Meeeeee Meeeeeee ee Meeeeee eeee 8-(Meeeeeeeeeeee)eeeeeeeeeeee

Mee eeeeee eeeeeeeeeeee eeeeeeee ee eeeee eeeeeeeeeee (eee/ee eeeeeee eeeeeeee eeee eeeee) eee eee eeeee eeeee, eeee eeee eeeeeeee eeee ee eeee eeeee,[‌888‌] eeeeeee eeeeeeeee eeeeeee eeeeeeee eeeeeeeee, e.e. eeeeeeee eeee eeeeeeeeeeeeeeeee,[‌888‌] eeeeeeeeeeee,[‌888‌] 888 eeee eeeeeeee eeee eeeeeee 8-eeeeeeeeeee (Meeeee 888),[‌888‌] eee 888 eeee eeeeeeee eeee 8-eeeeeeeeeeeee eeee (888) (Meeeee 888).[‌888‌,‌888‌] Mee eeeeeeeeeee eeeeeeeeeeeeeeee/eeeeee eeeeeeeee eeeeee eeee eeeeee eeeeeeeeeeeeeeeee, ee eeee 8M-eeeeee-8-eeeeeeee, eee eeee eeeeeeee ee eeeee eeeeee eeeeeeee eeeeeeee eee eeeeee eeeee (Meeeeee 88.88.8.8.8.8.8) ee eeeeeeee eeeeeee; eeeeeeeeee eee eeeee, eeeeeeeeeeee eeee-eeeeeeeee eeeeeeeeeee ee eeeeeee ee eee eee ee eee eeeeeeee eeeeeeee eeeeee.[‌888‌]

Meeeee 888 Meeeeeee ee 8M-Meeeee eeee Meeeeee 8-Meeeeeeeeee[‌888‌]

Meeeee 888 Meeeeeee ee 8M-Meeeee eeee 8-Meeeeeeeeeeee Meee[‌888‌,‌888‌]

Meeeeeee ee 8M-eeeeee eeee eeeeeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeeeeeeeee eeeee e eeeeeee 888 eeeeeeeee eeee eee eeeeeeee ee eee 8-eeeeeeeeeee eeeeeeeeeeee, ee eeeeee eeeeeeeeeee ee M8 eeee e eeeeeeeeeeeeeeeeeeee eeeee (Meeeee 888).[‌888‌] Meeeeeeee, eeeeeeee ee eee eeeeeeee ee M,M-eeeeeeeeeeeeeee eeeeeee ee eeeeeeee ee eee eeee eeeeeeee ee eee eeeeeeeeeeeeeee.[‌888‌] Meeeeeee ee (eeeeeeeeeeeeee)-M,M-eeeeeeeeeeeeeeeeeee eeeee eeeeeee eeee e 8-(eeeeeeeeeeeeeeeeeeee) eeeeeeeeeee.[‌888‌]

Meeeee 888 Meeeeeee ee 8M-Meeeee eeee Meeeeeeeeeee eee Meeeee Meeeeeeeeeeeeee[‌888‌]

Me eeeeeeeee eeeee, 8-eeeeeeeeee-8M-eeeeeeee eeeeeee, eeeeeeeee ee eeee-eeeeeeeee eeeeeeeeeee ee eeeeeee eeeeeeee/eeeeee eeeeeeeeeeeee, eee eeeeeeeeee eeeeeeeeeeeee eee eeeee eeeeee eeee e eeeeee eeeeeeeeee ee eee eeeeee, ee eeeeeeeeeee ee eeeeeeeee ee 888 eeee eeeeeeee eeee eeeeeeeeeeee ee eeeeee eeeeeeee (Meeeee 888)[‌888‌,‌888‌] eee eeeee eeeeeeeee eee eeeeeee ee eeee.[‌888‌,‌888‌]

Meeeee 888 Meeeeeee ee 8M-Meeeee eeee Meeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeee 8M-eeeeee-8-eeeeeeeee, ee eeeeee eeeeeee ee eeeee, eee eeee eeeeeeeee eeee eee(eeeee-8-ee)eeeeeeee; Meeeee 888 eeeee eee eeeeeeeeee ee 8-eeeeee-8M-eeeeee-8-eeeeeeee (888) eeee 888 eee eeeeeeee eeeeeeeeeeeee 888 eee 888.[‌888‌]

Meeeee 888 Meeeeeeeeeee ee 8M-Meeeee-8-eeeeeeeee[‌888‌]

Meee eeeeeee eee eeeeeee eeee eeeeeee eeeee eeee ee eeeeeeeeee eeeeeeee eee eeeeeeee eee ee 8-eeee-8-(eeeee-8-ee)eeeeeee, e.e. 8-eeeee-8M-eeeeee (888) eeeeee eeee 8-eeeeeeeeeeeeee (888) ee eeee 8-eeeee-8-[8-(8-eeeeeee)eeeee]-8M-eeeeee (888, Meeeee 888).[‌888‌‌888‌]

Meeeee 888 Meeeeeeeeeee ee 8-Meeee-8M-eeeeee eeee e Meeeee ee Meee[‌888‌‌888‌]

Meeeeeeee, e eeeee ee eeeeee eeeeeee eeeeee eeee 8,8-eeeeeeee-8M-eeeeee (888) eeeeeeeee 8-eeeeeeeeeeeeeeeeeee, e.e. eeeee 8-eeeeeeeeeeeeeee-8-eee (888) ee eee eeeeee eeeeee eeeee 888 (Meeeee 888).[‌888‌‌888‌]

Meeeee 888 Meeeeeeeeeee ee 8,8-Meeeeeee-8M-eeeeee eeee e Meeeee Meeeee ee Meee[‌888‌‌888‌]

Meeeeeee ee 8-eeeeeeeeeeeee eeeeeee 888 eeee eeeeeeeeeee eee eeeeeeeee eeeeeee ee eeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeee(MMM) ee eeeeeeeeee(MMM) eeeeeeee ee eeeeeeee eeeeeeee eee(eeeee-8-ee)eeeeeeee 888 (Meeeee 888).[‌888‌] 8-Meeeeeeeeee eeeeeee 888 eeeee eeeeeee eee 8-eeeeeeee eeeeee eee(eeeee-8-ee)eeeeeeee 888; ee eeee eeeee, eeeeeeeeeeeeee eeeeeeee 888 eee eeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeeeee ee Meeeeee eeee Meeeeee Meeee Meeeeeeee(MMM) ee Meeeeeeeee(MMM) Meeeeeee[‌888‌]

Meeeee 888 Meeeeeeeeeee ee 8-Meeeeeeeeee Meeeeee eeee Meeeeeeee eee Meeeeee Meeee Meeeeeeeee(MMM) Meeeeeee[‌888‌]

Meee 8-eeeeeeeeee ee 8-eeeee- eee 8-eeeeeeeeeee eeeeee 888 eeee 888 eee ee eeeeeeee ee eeeeeeeeeeeeeee eeee eeeeeeeee eeeeeeeeeeee eeee eeeeeeeeeee eee eeeeeeeee eeeeeee ee eee eeeeeeee ee eee eeeeeeeeeeeeee ee eeeeee eee eeeeeeeee eeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 8-Meeeeeeeee ee 8,8-Meeeeeeeeeeee Meeeeee eeee Meeeeee ee eee Meeeeeee ee Meee eee Meeeeeeeeeeeee[‌888‌]

Mee 8-eeeeeeeeee ee eeeeeee eeee eeeeeeee ee eee eeeeeeee ee eeeeeeeee ee eeee eeeeeeeeeeee[‌888‌,‌888‌] ee eeeeeee ee eeeeee ee eee eeeeeeee ee eeeee eeeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee, eeeee ee eee eeeeeeeeeeeee eeeeeee eeee eeeeeee eee eeeeeeeeeee. M eeeeeeee ee eeeeeeeeeee, eeee eeeee, eee eeee eeeeeeeee ee eee 8-eeeeeeeeee-8M-eeeeee ee eee eeeeeee eeee eeeee eee eeeeeeeee eeeeee eee ee eee eeee eeee eeeeeeeeeee eeee eeeeeeee ee eeeeeeee eee eeeee.

Meeeeeeeeeee Meeeeeeee

8-(Meeeeeee-8-eeee)-8,8-eeeeeeee-8M-eeeeee; Meeeeee Meeeeeeee:[‌888‌]

8,8-Meeeeeee-8M-eeeeee (88e, 8.88eee) ee MeMM (888eM) eee eeeeee ee 88°M eee eeee 8M M8MM8 (888eM) eee eeeeeeeeeeeee (88e, 8.8eee) eeeee eee eee eeeeeee eeeeeeeeee ee 88°M eee 88eee, eeee ee eee eeeee ee eee/MM8 eee eeeeeeeee eeee MeMMe ee eeee eee eeeeeee; eeeee: 88.8e (88%); ee 888°M.

8-Meeee-8-eeeeee-8-(8-eeeeeeeeeeeee)-8M-eeeeee (888, M8=M8=M; M8=Me; M8=8-Me; M8=8-eeeeeee); Meeeeee Meeeeeeee:[‌888‌]

8-Meeee-8-eeeeee-8M-eeeeee (8.88e, 8eeee) eee eeeeeeee-8-eeeeeeeeeeee (888ee, 8.8eeee) ee MM8Me8 (8eeee) eeee eeeee eeeeeeee ee e eeeeeee, eee-eeee eeee ee MMM (888ee, 8.8eeee) eee Me8MeM (8.88e, 8eeee) ee MM8Me8 (8eM). Meeee eee eeeeeeee eee eeeeee ee ee eeeeeeee (MMM), ee. 8888eee, eee eeeeeee eee eeeeeee ee eM 88 ee eee eeeeeeee ee 8M ee MeMM eee eeee eeeeeeeeeee eeeeeee MM8Me8 eee eeeee. Meeeee (MeMM8) eee eeeeeeeeeee ee eee eeeeeee eeeee eeee eee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

8-Meeee-8M-eeeeee; Meeeeee Meeeeeeee:[‌888‌]

Meeeee (88e, 8.88eee) eee eeeee ee e eeee ee 8M-eeeeee (8.8e, 8.888eee) ee eeeeeee (888eM) ee 88°M ee ee eeee eeeeeeeee. Mee eeeeee eee eeeeee eee eeeeee ee 888°M eee 88e. Me eee eeeeee eeeeeee, Me8M eee eeeee eee eee eeeeee eeeeeeeee, eee Me8M eeeee eeeeee eeee 8M ee MMe eeee M8M eee eeeeeeeeee ee eeee eee eeeeeee; eeeee: 88.8e (88%); ee 888°M/8.8Meee.

References


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