Vinyloxirane → HCID 14140997, compound

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Reaction Steps

40 ml of dry tetrahydrofuran and 20 ml of a 1.6 M n-butyl lithium solution were added to a nitrogen-substituted flask at −78° C., and the obtained mixture was then stirred for 30 minutes. Thereafter, 3.5 ml of a trifluoroborane tetrahydrofuran complex was slowly added dropwise to the reaction solution. The obtained solution was further stirred at −78° C. for 15 minutes, and 2.00 g of 1,3-butadiene monoepoxide was slowly added dropwise thereto. The thus obtained mixture was further stirred at −78° C. for 3 hours. Thereafter, 50 ml of a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained solution was extracted with 100 ml of ethyl acetate once and was then dried over sodium sulfate. The sodium sulfate was filtrated, and the organic layer was then concentrated. The residue was purified by flash chromatography (manufactured by Biotage AB; Isolera™), so as to obtain 1.80 g of 2-vinyl-4-phenyl-3-butyn-ol.

Provenance & Evidence