Oleoyl chloride → 1,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol

HRID 376421Notes

Reaction equation

HRID 376421 reaction equation
[Si:1]([O:8][CH:9]([CH2:12][OH:13])[CH2:10][OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:14](Cl)(=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>N1C=CC=CC=1>[C:14]([O:11][CH2:10][CH:9]([CH2:12][O:13][C:14](=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 5364783Oleoyl chlorideHCID 114811691,3-Propanediol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

Product 1

HCID 867518571,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 60 ml of pyridine was dissolved 2.75 g (0.013 mol) of 2-O-(t-butyldimethylsilyl)glycerol, followed by addition of 8.82 g (0.028 mol) of oleoyl chloride under ice-cooling. The reaction was conducted at 50° C. for 15 hours. After completion of the reaction, the solvent was distilled off and the residue was diluted with methylene chloride, washed with saturated aqueous sodium hydrogen carbonate solution, dried, and concentrated. The above procedure provided 1,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionthe residue was diluted with methylene chloride
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0f42cec5ba2f492b9cbef9a1444aaa68
Source dataset
uspto-grants-2000_02
Patent number
US06020317

Reaction notes

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