1,4-Dibromobutane → HCID 18612662, 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-phenyl-isoxazol-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 1,4-dibromobutane (358 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 (181 mg). Flash chromatography on silica gel (10% ethyl acetate in hexane) gave the product as a colorless oil (114 mg, 26.2%).

Provenance & Evidence