4-Toluenesulfonyl chloride → 3-O-Octadecyl-2-O-tosyl-1-O-tritylglycerol

HRID 1493863Notes

Reaction equation

HRID 1493863 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([OH:43])[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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].[S:44](Cl)([C:47]1[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=1)(=[O:46])=[O:45]>N1C=CC=CC=1>[CH2:1]([O:19][CH2:20][CH:21]([O:43][S:44]([C:47]1[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=1)(=[O:46])=[O:45])[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Product 1

HCID 135065293-O-Octadecyl-2-O-tosyl-1-O-tritylglycerolYield 83.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 9 ml of pyridine was dissolved 5.0 g (8.52 mmole) of 3-O-octadecyl-1-O-tritylglycerol, and after 1.95 g (10.22 mmole) of tosyl chloride was added to the solution, the mixture was stirred at room temperature overnight and concentrated to dryness under reduced pressure. The residue was dissolved in 50 ml of water and 50 ml of dichloromethane, and after shaking thoroughly, the dichloromethane layer was separated out. The organic layer was concentrated to dryness under reduced pressure, and the residue was purified by silica gel column (50 g), with n-hexane.ethyl acetate (193:7) used as an eluent, to give 5.3 g (yield of 83.9%) of colorless needles.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in 50 ml of water
  3. stirring50 ml of dichloromethane, and after shaking thoroughly
  4. customthe dichloromethane layer was separated out
  5. concentrationThe organic layer was concentrated to dryness under reduced pressure
  6. customthe residue was purified by silica gel column (50 g), with n-hexane

Sources & evidence

ORD record
ord-20cac1201ff846d9bb7df4bab31df42d
Source dataset
uspto-grants-1991_06
Patent number
US05025005

Reaction notes

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