[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].N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26].[NH4+].[Cl-]>C1COCC1.C(OCC)C>[CH2:1]([S:15][CH2:16][CH2:17][O:18][C:25](=[O:27])[CH3:26])[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]
2-Tetradecylsulfanyl-ethanol (0.54 g, 1.97 mmol) was dissolved in dry THF (10 ml) and pyridine (0.16 ml, 1.97 mmol) was added followed by acetyl chloride (0.15 m, 2.16 mmol). The resulting mixture was allowed to stir at ambient temperature for 23 hours, then another portion of acetyl chloride (0.075 ml, 1.08 mmol) and pyridine (0.080 ml, 0.95 mmol) was added. The mixture was stirred at ambient temperature for a further 90 minutes and then portioned between diethyl ether (30 ml) and 10% NH4Cl (30 ml). The organic layer was washed with brine (40 ml), dried (Na2SO4) and concentrated in vacuo. Toluene (10 mL) was added to the residue. The solvents were evaporated in vacuo and the crude product was purified by flash chromatography on silica gel (heptane:EtOAc 9:1) to afford 0.45 g (72%) of the title compound as a colorless solid.
Loading…
