[CH2:1]([S:15][CH2:16][C:17](O)=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1>[CH2:1]([S:15][CH2:16][CH2:17][OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]A solution of tetradecylsulfanyl-acetic acid (1.50 g, 520 mmol) in dry THF (10 ml) was added drop wise to a suspension of LiAlH4 (0.40 g, 10.4 mmol) in dry THF (30 ml) at 0° C. The mixture was stirred at 0° C. for one hour and then at ambient temperature for 18 hours. Saturated NH4Cl (40 ml) was added, and the resulting mixture was filtered through a short pad of celite. The phases were separated and the aqueous layer was extracted with diethyl ether (50 ml). The combined organic phases was washed with brine (50 ml), dried (Na2SO4) and concentrated in vacuo. Purification by flash chromatography on silica gel (heptane:EtOAc 4:1) afforded 0.76 g (54%) of the title compound as a colourless solid.
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