Oleyl p-toluenesulfonate → HCID 70256374, Verbindung

HRID 376416

Reaktionsgleichung

Reaktionsgleichung von HRID 376416
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[O:6][CH:7]([CH2:10][OH:11])[CH2:8][OH:9].[C:12](O[K])([CH3:15])([CH3:14])C.C1(C)C=CC(S(O[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:45]([O:11][CH2:10][CH:7]([CH2:8][O:9][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]/[CH:34]=[CH:33]\[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:14][CH2:12][CH3:15])[O:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]/[CH:37]=[CH:36]\[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28]

Komponenten

5

Edukt 3

HCID 11258749Oleyl p-toluenesulfonateHCID 19361256HCID 19361256, VerbindungHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 70256374HCID 70256374, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel2×

Versuchsvorschrift

In 30 ml of xylene was dissolved 854 mg (5.3 mmol) of 2-O-tetrahydrofuranylglycerol. To this was added 1.78 g (15.9 mmol) of t-butoxypotassium under argon gas and the mixture was stirred for 5 minutes. Then, 10 ml of a solution of 6.71 g (15.9 mmol) oleyl p-toluenesulfonate in xylene was added dropwise and the mixture was stirred under reduced pressure (20-30 mmHg) at ambient temperature for 30 minutes and further at 50° C. for 1 hour. This reaction mixture was poured in ice-water and extracted with ether, and the extract was washed with water, dried, and concentrated. The residue was purified by column chromatography (silica gel/chloroform) to provide 628 mg (18%) of 1,3-O-dioleyl-2-O-tetrahydrofuranylglycerol as yellow oil. (5) In 30 ml of tetrahydrofuran was dissolved 628 mg (0.95 mmol) of 1,3-O-dioleyl-2-O-tetrahydrofuranylglycerol followed by addition of 5 ml of diluted (10%) hydrochloric acid, and the mixture was stirred overnight. The reaction mixture was then diluted with water, neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ether. The extract was dried and concentrated and the residue was subjected to column chromatography (silica gel/n-hexane-ethyl acetate) to provide 321 mg (57%) of the title compound as colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred under reduced pressure (20-30 mmHg) at ambient temperature for 30 minutes and further at 50° C. for 1 hour
  2. extractionextracted with ether
  3. washthe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-462aa6735f5049069925dc7e93bf77c6
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020317

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