(R)-1,2-Epoxypropane → (R)-oct-7-en-2-ol

(R)-(+)-1,2-epoxypropane (1.12 ml, 16.0 mmol) is dissolved in dry THF (23 ml) and CuBr (230 mg, 1.6 mmol) is added therein, after which the temperature is reduced −78° C. The 1M 4-pentenylmagnesium bromide solution (23 ml, 23.5 mmol) prepared in the reaction (1) is added to reaction mixture. The temperature is gradually increased to a room temperature and the mixture is stirred for 4 hours. The reaction is finished with saturated NH4 Cl solution (10 ml). An obtained product is extracted with Et2O (20 ml×2) and it is washed by water (10 ml). An organic layer is dried using anhydrous MgSO4. The solution is vacuum concentrated, and then the compound (III) (1.3 g, 65%) is isolated using flash column chromatography (Et2O/n-pentene, 5:1, v/v):

1. customis reduced −78° C
2. additionis added to reaction mixture
3. extractionAn obtained product is extracted with Et2O (20 ml×2) and it
4. washis washed by water (10 ml)
5. customAn organic layer is dried
6. concentrationconcentrated

ORD record

ord-c2c1cc7bb8cc4a1ab217c17e7d14f650

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951839B2