Chloride → HCID 14877801, compound

HRID 478108Notes

Reaction equation

HRID 478108 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][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30]O)[O:22][CH3:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:32]([N:34](CC)[CH2:35]C)C.[Cl-]>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]([O:22][CH3:23])[CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:34]([CH3:35])[CH3:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 312ChlorideHCID 8471TriethylamineHCID 14877727HCID 14877727, compound

Product 1

HCID 14877801HCID 14877801, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.95 g (13.4 millimole) of 1-O-(12-cyclohexyldodecyl)-3-O-[2-(2-hydroxyethoxy)ethyl]-2-O-methylglycerol was dissolved in 30 ml of dichloromethane, to which 1.76 g (17.4 millimole) of triethylamine was added, and then 1.84 g (16.1 millimole) of methaneslfonyl chloride was added dropwise over a period of 30 minutes under ice cooling. The reaction mixture was stirred at the same temperature for 1 hour, washed with water, and dried over anhydrous magnesium sulfate. Dichloromethane was distilled off to give 7.0 g of colorless oil. 2.0 g of this product was dissolved in 10 ml of 20% dimethylamine in toluene, and stirred at room temperature overnight and then at 30° C. for 4 hours, and then concentrated under reduced pressure. To the residue were added 30 ml of dichloromethane and 10 ml of saturated aqueous solution of sodium hydrogencarbonate, and the mixture was shaken thoroughly. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to silica gel (50 g) column chromatography, and eluted with chloroform-methanol (6:1), to give the above-captioned compound as colorless oil. Yield: 1.5 g (83%).

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationDichloromethane was distilled off

Sources & evidence

ORD record
ord-dde33490706845d9b6bf20a6f797951b
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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