Tetrahydrofuran → HCID 178445630, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 25.2 g (73.5 mmol) of methoxymethyltriphenyl phosphonium chloride and 300 ml of THF was cooled to −50° C. under a gas stream of nitrogen. To the mixture, 7.6 g (67.8 mmol) of t-BuOK was added and stirred for 1 hour. To the mixture, a solution of 14.8 g (56.5 mmol) of trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl acetaldehyde in 150 ml of THF was added dropwise with maintaining the temperature below −50° C. After dropwise addition, the reaction temperature was increased gradually to the room temperature, and stirring was carried out further for 5 hours. The solvent was distilled off under a decresed pressure, 150 ml of water was added and the mixture was extracted with 200 ml of toluene. The organic layer was washed with 100 ml of water for three times and dried with anhydrous magnesium sulphate. The solvent was distilled off under a decreased pressure, and the residue was subjected to silica gel column chromatography (eluent: a mixed solvent of toluene/heptane=3/7), to obtain 12.8 g of crude 1-(3-methoxypropenyl)-trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexane.

Provenance & Evidence