反应详情

To a solution of0.11 g (0.21 mmol) of 1-benzyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde in 3 mL of THF were added 0.14 mL (0.42 mmol) of methyl magnesium bromide dropwise at 0° C. under an argon stream. The mixture was stirred at RT for 1.5 h and poured into a mixture of a saturated aqueous solution of NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 0.118 g (quantitative) of crude 1-[1-benzyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-1H-indol-2-yl]-ethanol, which was dissolved in 2 mL of THF and treated with 0.43 mL (0.43 mmol) of a 1M TBAF-solution in THF, stirred for one hour and then poured into a mixture of a saturated aqueous solution of NH4Cl and Et2O. The phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 0.066 g (74%) of 2-[1-benzyl-2-(1-hydroxy-ethyl)-1H-indol-5-yl]-1,1,1,3,3,3-hexafluoro-propan-2-ol, yellow solid, MS: 418 (M−H)−.

1. customThe phases were separated
2. extractionthe aqueous one was extracted with Et2O
3. dry with materialThe combined organic phases were dried over Na2SO4
4. customevaporated