Triethylamine → HCID 14877725, compound

Reaction equation

[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([CH2:24][OH:25])[O:22][CH3:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[S:33](Cl)([CH3:36])(=[O:35])=[O:34]>ClCCl>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([CH2:24][O:25][S:33]([CH3:36])(=[O:35])=[O:34])[O:22][CH3:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Procedure

To a mixture of 1.70 g (4.78 millimole) of 1-O-(12-cyclohexyl)dodecyl-2-O-methylglycerol, 580 mg (5.74 millimole) of triethylamine and 10 ml of dichloromethane, 657 mg (5.74 millimole) of mesyl chloride was added dropwise under ice cooling. After stirring for 1 hour under ice cooling, the reaction mixture was washed with water, saturated solution of sodium hydrogencarbonate, and water, successively, and dried (MgSO4), followed by evaporation of the solvent. The residue was subjected to silica gel (60 g) column chromatography, and eluted with hexane-ethyl acetate (5:1), to give the above-captioned compound as colorless solid. Yield: 1.93 g (97%).