[CH:1]1([CH:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:5][C:6](OC)=[O:7])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1([CH:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:5][CH2:6][OH:7])[CH2:3][CH2:2]1A stirred solution of 10.7 grams (0.045 mole) of methyl 3-cyclopropyl-3-(4-chlorophenyl)propanoate in 45 ml of tetrahydrofuran was cooled to 0° C., and 45 ml of 1.0 M of lithium aluminum hydride in tetrahydrofuran was added slowly during a one hour period. Upon completion of addition, the reaction mixture was stirred at 0° C. for two hours and then was allowed to warm to ambient temperature. The reaction was quenched by the sequential addition of 2 ml of water, 2 ml of aqueous 15% sodium hydroxide, and 6 ml of water. The reaction mixture was taken up in 100 ml of diethyl ether. The solution was filtered, and the filtrate was dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 9.3 grams of 3-cyclopropyl-3-(4-chlorophenyl)propan-1-ol.
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