Diisopropylethylamine → 7-Iodo-5-nitro-3-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-benzoxazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 7-iodo-5-nitro-1,3-benzoxazol-2(3H)-one (0.76 g, 2.5 mmol) in N,N-dimethylformamide (5 mL) at 0° C. was treated with N,N-diisopropylethylamine (0.65 mL, 3.7 mmol) followed by [β-(trimethylsilyl)ethoxy]methyl chloride (0.61 mL, 3.5 mmol) dropwise and stirred at 20° C. for 1 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with 0.5 M HCl (50 mL), brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to a crude oil. This material was purified by flash column chromatography to give the desired product (0.93 g, 86%) as a yellow oil.

Provenance & Evidence