Ethyl bromoacetate → HCID 70025487, compound

Participants

Reaction Steps

Charged flask with a 60% sodium hydride in oil dispersion (64.0 mg, 1.6 mmol) and suspended in DMF (1 ml). A DMF (1 ml) solution of naphthalen-1-ylmethyl-(3-phenylisoxazol-5-yl)-amine (300 mg, 1.0 mmol ) was added and the mixture stirred under argon at rt for 30 min resulting in a light yellow solution. After adding ethyl bromoacetate (333 μl, 3.0 mmol), the reaction was stirred at rt for 1 hr, poured into 10% sodium bicarbonate (aq) and extracted with ethyl acetate (3×). The extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a crude oil (370 mg). Flash chromatography on silica gel (15% ethyl acetate in hexane) gave the title compound as a colorless oil (306 mg, 73.9%).

Provenance & Evidence