Tetrabutylammonium Fluoride → Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)but-2-enoate

Participants

Reaction Conditions

Reaction Steps

1.3.11 g of tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2-ethylbut-2-enoate are dissolved in 20 ml of tetrahydrofuran, and 15.7 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran are added. The mixture is stirred at 60° C. for 2 hours. The reaction mixture is concentrated under reduced pressure and purified on silica gel using the mobile phase n-heptane:ethyl acetate=30:1=>ethyl acetate. This gives 1.65 g of tert-butyl 2-ethyl4-(cis-3-hydroxycyclohexyl]but-2-enoate as an oil. C16H28O3 (268.40), Rf(n-heptane:ethyl acetate=5:1)=0.07.

Provenance & Evidence