反応 #604079

反応方程式

tetrabutyl ammonium fluoride

dimethyl 2-(4-((tert-butyldimethylsilyl)oxy)benzyl)-3-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)maleate

→

title compound

収率 80.0%

Dimethyl 2-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-3-(4-hydroxybenzyl)maleate

収率 80.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他The solvent was removed by distillation under reduced pressure
2. 2
   その他the residue was chromatographed on silica gel column (hexane:ethyl acetate=85:15)

実験手順

A 1.0 M tetrabutyl ammonium fluoride solution in THF (0.29 ml, 0.29 mmol) was added dropwise to a solution of dimethyl 2-(4-((tert-butyldimethylsilyl)oxy)benzyl)-3-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)maleate (55 mg, 0.10 mmol) in THF (1.0 ml) at 0° C., and the mixture was stirred at room temperature for 5 hr. The solvent was removed by distillation under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate=85:15) to give the title compound as a yellow oil (35 mg, yield 80%).

出典