TBAF tetrahydrofuran → 1,3-Diolein

HRID 376422Notes

Reaction equation

HRID 376422 reaction equation
[C:1]([O:20][CH2:21][CH:22]([CH2:31][O:32][C:33](=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[O:23][Si](C(C)(C)C)(C)C)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[C:1]([O:20][CH2:21][CH:22]([CH2:31][O:32][C:33](=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[OH:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 867518571,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol

Product 1

HCID 54971651,3-Diolein

Procedure

To 1,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol was added 266 ml of 0.1 M tetra-n-butylammonium fluoride-tetrahydrofuran and the reaction was carried out at ambient temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was diluted with methylene chloride, washed with water, dried, and concentrated. The residue was subjected to column chromatography (silica gel/ethyl acetate-n-hexane) to provide 3.97 g (48.0% based on 2-O-t-butyldimethylsilylglycerol) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with methylene chloride
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-845078eec786490180be1ea4866c4c03
Source dataset
uspto-grants-2000_02
Patent number
US06020317

Reaction notes

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