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

HRID 854716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854716
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 99475821-o-Oleoyl-2-o-methyl-rac-glycerolAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1M TBAF (6 mL, 6.0 mmol) was added to a solution of compound Compound 43 (2.4 g, 5.0 mmol) in THF (50 mL). After 30 nun, TLC analysis showed that all the staring material had been consumed. Then, the reaction mixture was partitioned between diethyl 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 Compound 44 (1.52 g, 79%) as an oil

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-667586cdc909428a980476ce4b259f10
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259273B1

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