Science of Synthesis

Grosjean, C.; Whiting, A., Science of Synthesis, (2008) 36, 261.

The addition of organolithium compounds to carboxylic acids, to afford tertiary alcohols, has not been widely reported. Two examples are shown in ‌Scheme 12‌. Addition of the organometallic compound is generally performed in tetrahydrofuran or diethyl ether. Successive addition of the alkyllithium to the acid ‌26‌ at low temperature affords the alcohol ‌27‌ in 82% yield.[‌27‌] Direct addition of acid ‌28‌ to a solution of methyllithium results in the formation of the ketone ‌29‌ and the alcohol ‌30‌ in similar quantities.[‌28‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeeeeee Meeeeeee ee Meeeeeeeee Meeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee:

(8M)-8-[(8eM,8M,8eM)-8-(eeee-Meeeeeeeeeeeeeeeeee)eeeeeeeee-8eM-eeeee-8e-ee]-8-eeeeeeeeee-8-ee-8-ee (‌88‌):[‌88‌]

8.88 M MeMe ee Me8M (8 eM) eee eeeee eeeeeee ee e eeeeee eeee ee eee eeee ‌88‌ (8.88 e, 8.88 eeee) ee MMM (8 eM) ee 8°M. Mee eeeeeee eee eeeeeee ee ee eee 8 e. Mee eeeeeeee eee eeeeeeee eeee M8M (88 eM) eee eeeeeeeee ee eM 8–8 eeee 8% MMe. Mee eeeeeee eeeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeeee eeee eeeeee eeee eee. ee MeMe (88 eM), eeeee, eeeeeeee, eeeeeeeeeeee, eee eeeee eeeee eeee eeeeee. Mee eeeeeee eee eeeeeeeee ee MMM (8 eM) eee 8.88 M MeMe ee Me8M (8 eM) eee eeeee ee eee eeeeee eeee ee −88°M. Mee eeeeeee eee eeeeeee eee 88 e. Mee eeeeeeee eee eeeeeeee eeee M8M (88 eM) eee eee eeeeeee eeeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeeee eeee eeeeee eeee eee. ee MeMe (88 eM), eeeee, eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (88 × 8.8 ee, MeMMe/eeeeeee 8:88) ee eeee eee eeeeeee ‌88‌ ee e eeeeeeeee eee; eeeee: 8.88 e (88%).

References