Tetrabutylammonium Fluoride → (S)-ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Participants

Reaction Steps

To a solution of (S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (260 mg, 0.5 mmol) in anhydrous THF (4 mL) at 0° C. was added a 1N tetrabutylammonium fluoride in THF (0.6 mL, 0.6 mmol) and stirred for 1 hour. The reaction was quenched by the addition saturated NaHCO3 solution and extracted using EtOAc. The organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 5 to 30% ethyl acetate/hexanes) to give the desired compound. LCMS-ESI− (m/z): [M−H]− calcd for C19H22BrO4: 394.29. Found: 394.0.

Provenance & Evidence