Hydride → (2R,6R)-(+)-2,6,10-trimethylundecan-1-ol

Participants

Reaction Steps

2(R),6(R),10-trimethylundecanoic acid methyl ester (172 mg., [α]D25 -11.30°) and lithium aluminum hydride (170 mg.) in absolute ether (20 ml.) were refluxed with stirring for 2 1/2 hours. The reaction mixture was cooled in an ice-bath and excess of hydride was destroyed by carefully adding water followed by 30 ml. of 1 N aqueous H2SO4. The aqueous phase was extracted with ether (3 × 40 ml.) and the combined ether extract was washed with water (3 × 30 ml.) and dried (MgSO4). The crude product (155 mg.) was purified by evaporative distillation to give 152 mg. (100% yield) of 2(R),6(R),10-trimethylundecan-1-ol as a colorless liquid, b.p. 100°-102° C./0.08 mm Hg.; [α]D25 + 6.09° C. (c 2.0366, hexane).

Provenance & Evidence