Benzenesulfonyl chloride → (rac)-1-O-octadecyl-2-O-benzenesulfonyl-3-O-trityl-glycerol

HRID 638532Notes

Reaction equation

HRID 638532 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:22])[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].[C:44]1([S:50](Cl)(=[O:52])=[O:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>N1C=CC=CC=1.ClCCl.C(Cl)(Cl)Cl>[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:22][S:50]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=[O:52])=[O:51])[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

6

Reactant 2

HCID 7369Benzenesulfonyl chloride2×HCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Product 1

HCID 92035207(rac)-1-O-octadecyl-2-O-benzenesulfonyl-3-O-trityl-glycerolYield 98.9%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (rac)-1-O-octadecyl-3-O-trityl-glycerol (30.52 g) in a mixture of pyridine (41.08 g) and dichloromethane (250 ml) was dropwise added a solution of benzenesulfonyl chloride (18.36 g) in chloroform (50 ml) during a period of 10 minutes below 10° C. After stirring for 2 days at ambient temperature, the reaction mixture was refluxed for 8 hours. To the reaction mixture, were dropwise added pyridine (12.75 g) and benzenesulfonylchloride (5.7 g) successively. After stirring for 2 hours at room temperature, the reaction mixture was allowed to stand for 2 days. The reaction mixture was washed with water, 0.5N aqueous sulfuric acid, water, aqueous sodium bicarbonate and water, successively. The solution was dried over magnesium sulfate and evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (450 g, elution by benzene) to give 37.4 g of (rac)-1-O-octadecyl-2-O-benzenesulfonyl-3-O-trityl-glycerol as an oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 8 hours
  2. stirringAfter stirring for 2 hours at room temperature
  3. waitto stand for 2 days
  4. washThe reaction mixture was washed with water, 0.5N aqueous sulfuric acid, water, aqueous sodium bicarbonate and water
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give a residue, which
  8. customwas purified by column chromatography on silica gel (450 g, elution by benzene)

Sources & evidence

ORD record
ord-90069915e3a74fe2a9e9edfccd97c963
Source dataset
uspto-grants-1985_12
Patent number
US04562179

Reaction notes

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