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

HRID 1906194Notes

Reaction equation

HRID 1906194 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 millimoles) of 3-O-octadecyl-1-O-tritylglycerol, and 1.95 g (10.22 millimoles) 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, the dichloromethane layer was separated. The organic layer was concentrated to dryness under reduced pressure and the residue was purified by silica gel (50 g) column chromatography using n-hexaneethyl acetate (193:7) as an eluent to give 5.3 g (83.9%) of colorless needles.

Workup

  1. additionwas added to the solution
  2. concentrationconcentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of water
  4. stirring50 ml of dichloromethane and, after shaking
  5. customthe dichloromethane layer was separated
  6. concentrationThe organic layer was concentrated to dryness under reduced pressure
  7. customthe residue was purified by silica gel (50 g) column chromatography

Sources & evidence

ORD record
ord-297156aff11b48339f38a69001e6ad5e
Source dataset
uspto-grants-1987_03
Patent number
US04650791

Reaction notes

Loading…