[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Si]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[CH:45][C:44]=1[Cl:54])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.O>O1CCCC1>[Cl:54][C:44]1[CH:45]=[C:46]([CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH:47]=[CH:48][C:43]=1[CH2:42][OH:41]A solution (1.0 M, 2.4 ml) of tetrabutylammonium fluoride/tetrahydrofuran was added to a solution of 1-((tert-butyldiphenylsilyloxy)methyl)-2-chloro-4-(n-pentyl)benzene (890 mg) in tetrahydrofuran (4.5 ml) under ice-cooling, and the mixture was stirred for 2 hr. Water was added to the reaction mixture and the resulting product was extracted three times with ethyl acetate. The organic layers were combined and washed successively with diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1) to give the objective compound (345 mg) as a colorless oil.
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