C([O:3][C:4](=O)/[CH:5]=[CH:6]/[CH2:7][CH2:8][C:9]([F:12])([F:11])[F:10])C.[H-].C([Al+]CC(C)C)C(C)C.Cl>C(OCC)C.CCCCCC>[F:10][C:9]([F:12])([F:11])[CH2:8][CH2:7][CH2:6]/[CH:5]=[CH:4]/[OH:3]A solution of 10 g of 6,6,6-trifluoro-2-transhexenoic acid ethyl ester (see above) in 70 ml of diethyl ether is cooled to 0°-5° and at this temperature 102 ml of 1M diisobutylaluminium hydride solution in hexane are added. The reaction mixture is then stirred for 5 minutes at 0°-5° and carefully hydrolysed with approx. 200 ml of 6N hydrochloric acid. The organic phase is separated off and the aqueous phase is extracted a further 3 times with ether. The combined organic phases are dried over MgSO4, and concentrated by evaporation. Chromatography of the residue on silica gel with hexane/ethyl acetate (7:3) yields the title compound in the form of a colourless liquid.
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