Tetrabutylammonium Fluoride → 1-o-Oleoyl-2-o-methyl-rac-glycerol

HRID 843570Notes

Reaction equation

HRID 843570 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH:28]([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:29][CH3:30])(C(C)(C)C)(C)C>C1COCC1>[C:33]([O:32][CH2:31][CH:28]([CH2:27][OH:26])[O:29][CH3:30])(=[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]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 877595431-o-t-Butyldimethylsilyl-2-o-methyl-3-o-oleoyl-rac-glycerol

Product 1

HCID 99475821-o-Oleoyl-2-o-methyl-rac-glycerolYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1M TBAF (6 mL, 6.0 mmol) was added to a solution of compound 16 (2.4 g, 5.0 mmol) in THF (50 mL). After 30 min, TLC analysis showed that all the starting material had been consumed. Then, the reaction mixture was partitioned between diethy ether (100 mL and sat. NaCl solution (30 mL). The organic extract was dried (MgSO4), concentrated and subjected to silica-gel column chromatography (eluent: hexane/ethyl acetate, 75/25, v/v] to give glycerol derivative 17 (1.42 g, 79%) as an oil

Workup

  1. customhad been consumed
  2. customThen, the reaction mixture was partitioned between diethy ether (100 mL and sat. NaCl solution (30 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d1288e1eb4b443edb0cb69bf1190ac6a
Source dataset
uspto-grants-2002_04
Patent number
US06380177B1

Reaction notes

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