[CH3:1]/[C:2](/[CH2:8][CH2:9][CH2:10][C:11]([CH3:13])=[CH2:12])=[CH:3]\[C:4](OC)=[O:5].C1C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>CO>[CH3:1]/[C:2](/[CH2:8][CH2:9][CH2:10][C:11]([CH3:13])=[CH2:12])=[CH:3]\[CH2:4][OH:5]To a mixture of the foregoing dienoic ester (0.827 mmol) and 7.5 ml of benzene, under nitrogen, is added 1.5 ml of 1.78 M diisobutyl aluminum hydride (DIBAH). After about 2 hours, 1 ml more of DIBAH is added and the reaction continued to completion as checked by thin layer chromatography. The reaction is worked up by adding about 2 ml of methanol and dilute HCl. The aqueous layer is extracted with ether. Then the combined ether phases are washed with water and brine, dried over sodium sulfate and solvent evaporated to yield (E)-3,7-dimethyl-2,7-octadien-1-ol.
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