Methanol → [2-Fluoro-4-(4-hydroxy-cyclohex-1-enyl)-phenyl]-carbamic acid benzyl ester

Participants

Reaction Steps

{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-2-fluoro-phenyl}-carbamic acid benzyl ester (340 mg, 0.75 mmol) was dissolved in THF (10 mL). To this solution at rt was added TBAF (1M in THF) (2 mL, 2 mmol). The reaction mixture was stirred at rt overnight. After the reaction was complete (TLC, 5% MeOH in DCM), the reaction was diluted with EtOAc (5 mL), quenched with NaHCO3 (saturated, 5 mL). The two layers were separated and the aq. layer was extracted with EtOAc (15 mL×2). The EtOAc solution was combined, washed with NaHCO3 aq, and brine (10 mL each), sequentially, and dried over K2CO3, filtered, concentrated. The crude product was purified on a silica gel column, eluted with 5% MeOH in DCM to obtain 230 mg (92% yield) of the title compound as a tan solid.

Provenance & Evidence