[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(/[CH:13]=[CH:14]/[C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][C:31](OCC)=[O:32])=[CH:24][CH:23]=3)[N:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O1CCCC1.Cl>C(OCC)C.O>[C:7]1(/[CH:13]=[CH:14]/[C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][OH:32])=[CH:26][CH:27]=3)[N:19]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
To a suspension of lithium aluminum hydride (350 mg) in diethyl ether (10 ml) was added dropwise, at 0° C., a solution of ethyl 4-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]butyrate (3.00 g) in diethyl ether (10 ml)—tetrahydrofuran (10 ml). The mixture was stirred at 0° C. for one hour and at room temperature for further one hour, followed by addition of water. The mixture was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:1,v/v), 4-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]butanol (2.00 g, 74%) was obtained. Recrystallization from ethyl acetate-hexane afforded colorless needles, mp 90-91° C.
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