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

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.

1. temperatureThe reaction mixture was cooled to 0° C.
2. temperatureThe resulting mixture was warmed to ambient temperature
3. stirringstirred for four hours
4. customThe reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride
5. extractionThe aqueous fraction was back-extracted with methylene chloride
6. dry with materialdried over sodium sulfate
7. customThe desired title intermediate was further purified by liquid chromatography

ORD record

ord-e16c55e26d094e7caf5e90fafad83940

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1