Vinyloxirane → HCID 14140997, compound

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.

1. additionThereafter, 3.5 ml of a trifluoroborane tetrahydrofuran complex was slowly added dropwise to the reaction solution
2. stirringThe obtained solution was further stirred at −78° C. for 15 minutes
3. stirringThe thus obtained mixture was further stirred at −78° C. for 3 hours
4. extractionthe obtained solution was extracted with 100 ml of ethyl acetate once
5. dry with materialwas then dried over sodium sulfate
6. filtrationThe sodium sulfate was filtrated
7. concentrationthe organic layer was then concentrated
8. customThe residue was purified by flash chromatography (manufactured by Biotage AB; Isolera™)

ORD record

ord-72726f4e1180409dacc99945f574cfa0

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586505B2