C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]([F:16])([F:15])[CH2:8][CH2:9][C:10](OCC)=[O:11])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C(OCC)C.C(OCC)(=O)C>[F:15][C:7]([F:16])([CH2:8][CH2:9][CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][OH:3]
To a solution of 4,4-difluoro-heptanedioic acid diethyl ester (1.3 g, 5.65 mmol) in diethyl ether (35 ml) at 0° C. under N2 was slowly added solid LAH (638 mg, 11.80 mmol). The resulting mixture was allowed to stir for 30 mins at room temperature and then heated to reflux for two hours. Upon cooling, water (0.5 ml) was added, followed by 15% NaOH (0.5 ml) and water (1.5 ml). The resulting mixture was stirred for another two hours at room temperature and then diluted with ethyl acetate (500 ml). The organic solution was dried over Na2SO4 without aqueous work-up. Evaporation of the solvent gave the title compound (646 g, 68%) as pure colorless oil. 1H NMR (CDCl3) δ 1.71–1.80 (m, 4H), 1.87–2.03 (m, 4H), 3.69 (t, 4H, J=60 Hz); 19F NMR (CDCl3) δ −22.64–22.28(m); 13C NMR (CDCl3) δ 25.81, 25.87, 25.92, 32.99, 33.33, 33.67, 122.38, 125.56, 128.74.
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