Methanol → 2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanone

反応式

C[OH:2].[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=C)[CH:13]([F:27])[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:2])[CH:13]([F:27])[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

実験手順

A methanol (300 mL) solution of [1-({[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}methyl)vinyl]benzene (2.02 g, 5.95 mmol) was cooled to −70° C. Ozone gas was bubbled through the solution until a blue color appeared. The solution was purged with nitrogen then a solution of triphenylphosphine (2.34 g, 8.92 mmol) in methylene chloride (100 mL) was added. Contents of the reaction flask were warmed to room temperature and the solvent was removed under reduced pressure. The remaining residue was subjected to flash column chromatography (hexane:ethyl acetate, 90:10) to give 2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanone as a colorless oil (1.68 g, 83% yield).