Triethylamine → HCID 14877725, compound

HRID 478101Notes

Reaction equation

HRID 478101 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

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 147189253-[(12-Cyclohexyldodecyl)oxy]-2-methoxypropan-1-ol

Product 1

HCID 14877725HCID 14877725, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%).

Workup

  1. additionwas added dropwise under ice cooling
  2. washthe reaction mixture was washed with water, saturated solution of sodium hydrogencarbonate, and water
  3. dry with materialsuccessively, and dried (MgSO4)
  4. customfollowed by evaporation of the solvent
  5. washeluted with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-e62d9de1a9714e31bbefb6c05e4a5e65
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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