Triethylamine → HCID 20034824, compound

HRID 231276Notes

Reaction equation

HRID 231276 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([O:31][CH3:32])[CH2:22][S:23]([CH2:26][CH2:27][CH2:28][CH2:29][OH:30])(=[O:25])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>ClCCl>[CH2:1]([O:19][CH2:20][CH:21]([O:31][CH3:32])[CH2:22][S:23]([CH2:26][CH2:27][CH2:28][CH2:29][O:30][S:34]([CH3:33])(=[O:36])=[O:35])(=[O:25])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20034829HCID 20034829, compound

Product 1

HCID 20034824HCID 20034824, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane is dissolved 2.5 g of 4-[(3-octadecyloxy-2-methoxypropyl)sulfonyl]butanol, to which 0.78 g of methanesulfonyl chloride and 0.95 ml of triethylamine are added dropwise with stirring under ice cooling. After being stirred at room temperature for 40 minutes, the mixture is washed with water, an aqueous sodium bicarbonate solution and water, and dried. The solvent is distilled off under reduced pressure to leave 2.76 g of 4-mesyloxybutyl 3-octadecyloxy-2-methoxypropyl sulfone. This is dissolved in 40 ml of toluene containing 8 g of trimethylamine, and the solution is stirred at room temperature for 40 hours. The reaction mixture is concentrated and reprecipitated from chloroform-acetone to give 2.1 g of the captioned compound.

Workup

  1. stirringAfter being stirred at room temperature for 40 minutes
  2. washthe mixture is washed with water
  3. dry with materialan aqueous sodium bicarbonate solution and water, and dried
  4. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-483abcdc729d47fa8a0083eeb16de58f
Source dataset
uspto-grants-1989_07
Patent number
US04845219

Reaction notes

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