Tetrahydrofuran → HCID 59497429, compound

Participants

Reaction Steps

5-Chloro-2-oxo-2,3-dihydro-benzooxazole-7-carboxylic acid methyl ester (8 g, 35 mmol) is suspended in diethyl ether (100 mL) and tetrahydrofuran (410 mL) and cooled to zero. The reaction is purged with nitrogen and LiBH4 (6.72 g, 310 mmol) is added portion wise to the reaction. The reaction is warmed to room temperature and stirred for 3 hours. Upon completion the reaction is cooled to 0° C. and quenched by the slow addition of saturated ammonium chloride (250 mL). Water is added to the reaction (500 mL) and the organic layer separated. The water layer is extracted with ethyl acetate (3×100 mL) and the combined organic layers are dried (Na2SO4) filtered and evaporated in vacuo. Product is purified on silica with dichloromethane methanol as the eluent to yield (4.2 g 31 mmol 60%) the title compound (4.2 g 31 mmol 60%). LCMS (ESMS): m/z 200.5 (M+H+).

Provenance & Evidence