Acetonitrile → HCID 178442135, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 6.56 g of compound (r-12) was dissolved into a mixed solvent of 100 mL of dichloromethane and 100 mL of acetonitrile, 3.91 g of triethylsilane was added thereto, and then 4.13 g of trifluoroborane-diethyl ether complex was added dropwise at −50° C., the resultant mixture was stirred at −78° C. for 30 minutes, and then stirred at room temperature for 1 hour. A saturated aqueous solution of sodium hydrogencarbonate was added dropwise to terminate a reaction, the resultant mixture was subjected to extraction with dichloromethane, and then organic layers were combined, the resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and then dried over anhydrous magnesium sulfate. A solvent was evaporated under reduced pressure, and the resultant residue was purified by fractionation on silica gel column chromatography (eluate:heptane), and further purified by recrystallization from ethyl acetate, and dried, and thus 1.11 g of 3-(4-(trans-4-propylcyclohexyl)-6-pentylcyclohexene (compound (1-1-1-3)) was obtained.

Provenance & Evidence