Tetrabutylammonium Fluoride → Rac-[1-(4-chloro-phenyl)-2-(4-hydroxy-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 1.37 g (2.88 mmol) rac-[2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(4-chloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester in 30 ml methanol were added at ambient temperature 3.45 ml (3.45 mmol) 1M tetrabutylammonium fluoride in tetrahydrofuran. After 10 min the reaction mixture was diluted with diethyl ether, the solution washed twice with sodium bicarbonate solution and once with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash-chromatography over silica gel with a heptane/ethyl acetate gradient of 0 to 80% ethyl acetate. The purified title compound was triturated in di-isopropyl ether, filtered, dried and obtained as colorless solid: MS (ISN): 360.2 (M−H)−.

Provenance & Evidence