Lithium hydride → 4-[(Benzyloxy)methyl]-6-bromo-2H-1,4-benzoxazin-3(4H)-one

Participants

Reaction Steps

In N,N-dimethylformamide (4 ml) was dissolved 6-bromo-2H-1,4-benzoxazin-3(4H)-one (200 mg, 0.88 mmol). The solution was cooled in an ice bath, the reaction vessel was charged with nitrogen gas, lithium hydride (purity 90%, 11.7 mg, 1.32 mmol) was then added thereto and the mixture was stirred at room temperature for 10 minutes. Thereafter, benzyl chloromethyl ether (0.20 ml, 1.44 mmol) was added dropwise to the reaction solution at the same temperature and the mixture was stirred at the same temperature for 1.5 hours. Thereafter, lithium hydride (purity 90%, 2.3 mg, 0.26 mmol) and benzyl chloromethyl ether (0.04 ml, 0.29 mmol) were added while continuing stirring, whereby the reaction was quenched. The reaction solution was diluted with dichloromethane, washed with water (×4), dried over anhydrous magnesium sulfate and filtered, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 278 mg (91%) of the title compound in the form of a white solid.

Provenance & Evidence