Water → 3-Methoxy-4-{4-[4-(trifluoromethyl)phenoxy]phenoxy}pent-2-en-1-ol

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:25]=[CH:24][C:11]([O:12][CH:13]([CH3:23])[C:14]([O:21][CH3:22])=[CH:15][C:16](OCC)=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[H-].O>CCOCC>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:25]=[CH:24][C:11]([O:12][CH:13]([CH3:23])[C:14]([O:21][CH3:22])=[CH:15][CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:26][CH:27]=1

Participants

Procedure

To a slurry of LiAIH4 (100 mg) in anhydrous ether (20 ml) is added dropwise at 0°, a solution of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoate (500 mg) in ether. After addition is complete, the reaction mixture is stirred for about 20 minutes. Excess of the hydride is decomposed using wet ether and water. Filtration and evaporation of filtrate gives the C-1 alcohol, 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-penten-1-ol, MS m/e 440 (M+).