C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:33]=[CH:32][C:15]([O:16][CH2:17][CH:18]([O:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:14][CH:13]=1>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH:18]([O:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])=[CH:32][CH:33]=1Oxalyl chloride (2.9 ml, 33.6 mmol) is added to 25 ml of methylene chloride and cooled to −78° C. Dry dimethyl sulfoxide (4.7 ml, 67.2 mmol) is then added and the reaction is stirred at −78° C. After 45 minutes, (±)-7-(4-fluorophenoxy)-6-(2-methoxyethoxymethoxy)-heptan-1-ol 44 (3.7 g, 11.2 mmol) dissolved in CH2Cl2 is added and the reaction is stirred at −78° C. After 1 hour, the reaction is quenched with 15.7 ml of triethylamine and diluted with CH2Cl2. The reaction mixture is then washed with water, brine dried (Na2SO4) and concentrated. The crude product is purified on silica gel (ethyl acetate:hexane 1:9) to give (±)-7-(4-fluorophenoxy)-6-(2-methoxyethoxymethoxy)-heptan-1-al 45, 3.3 g, 89%.
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