[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[CH:8]=[CH:9]/[C:10](OC)=[O:11])=[CH:2]1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C(OCC)(=O)C.O>[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[CH:8]=[CH:9]/[CH2:10][OH:11])=[CH:2]146 mg of methyl (E,E)-5-(3-thienyl)-2,4-pentadienoate was dissolved in 1 ml of tetrahydrofuran, and 0.59 ml of a 1M toluene solution of diisobutylaluminum hydride was added dropwise at -40° C. Water, 0.6 ml of 1N hydrochloric acid and ethyl acetate were added to the solution , and the organic layer separated was worked up in a customary manner to give 40 mg of (E,E)-5-(3-thienyl)-2,4-pentadien-1-ol as a colorless oil.
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