2-Butene-1,4-diol → HCID 59958665, compound

Participants

Reaction Steps

In a 500 ml flask, 1,4dihydroxybut-2-ene (6.13 ml, 74.5 mmol) was dissolved in N,N-dimethylformamide (150 ml) under a nitrogen atmosphere. Sodium hydride (60%, 2.98 g, 74.5 mmol) was added and the resulting mixture was stirred at ambient temperature for thirty minutes. The reaction mixture was cooled to 0° C. and 2-fluoro-5-bromobenzyl bromide (3.99 g, 14.9 mmol) was added dropwise. The resulting mixture was warmed to ambient temperature and stirred for four hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back-extracted with methylene chloride. The organic fractions were combined and dried over sodium sulfate. The desired title intermediate was further purified by liquid chromatography.

Provenance & Evidence