Chloride → 1-Methoxymethylene-4-(3-propylcyclopentyl)cyclohexane
Reaction equation
[Cl-].CC([O-])(C)C.[K+].[CH2:8]([CH:11]1[CH2:15][CH2:14][CH:13]([CH:16]2[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)[CH2:12]1)[CH2:9][CH3:10].C1[CH2:27][O:26][CH2:25]C1>>[CH3:25][O:26][CH:27]=[C:19]1[CH2:20][CH2:21][CH:16]([CH:13]2[CH2:14][CH2:15][CH:11]([CH2:8][CH2:9][CH3:10])[CH2:12]2)[CH2:17][CH2:18]1Participants
5
Procedure
THF (100 ml) was added to methoxymethyltriphenylphophnium chloride (29.3 g) in a reaction vessel under an atmosphere of nitrogen, and the solution was cooled to −15° C. t-BuOK (10.5 g) in a THF (50 ml) solution was added, and the stirring was continued for another 1 hour. 4-(3-Propylcyclopentyl)-cyclohexanone (15.0 g) in a THF (50 ml) solution was added dropwise, and the stirring was continued for another 2 hours. The reaction mixture was warmed to room temperature and was extracted with toluene after the addition of water (200 ml) The resulting organic layer was washed with water and dried over anhydrous sulfate, and the toluene was concentrated to a volume of about 100 ml under reduced pressure. The concentrate was poured into n-hexane (500 ml) and solids deposited were filtered off. The solvent of the resulting solution was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume) to give 1-methoxymethylene-4-(3-propylcyclopentyl)cyclohexane (17.0 g).