CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)/[CH:21]=[C:22](\[C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=1)/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C.O>C1COCC1>[Br:35][C:32]1[CH:31]=[CH:30][C:29](/[C:22](/[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:21]\[CH2:20][OH:19])=[CH:34][CH:33]=1A 1.2 M solution of DIBAL-H in toluene (84 ml, 100 mmol) was added dropwise, at −15° C. over 20 min, to a stirred solution of (Z)-3-(4-bromophenyl)-3-phenylacrylicacid ethyl ester (11.1 g, 33.5 mmol) in dry THF (150 ml), and the mixture stirred for 30 min. Rochelles salt and water was carefully added, and the resulting mixture extracted with ethyl acetate (x2). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give 9.3 g of (Z)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-ol.
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