3-Trityloxypropane-1,2-diol → 1,2-O-dioleyl-3-O-tritylglycerol

HRID 376410

Reaktionsgleichung

Reaktionsgleichung von HRID 376410
[C:1]([O:20][CH2:21][CH:22]([CH2:24][OH:25])[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](O[K])([CH3:29])([CH3:28])C.C1(C)C=CC(S(O[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:59]([O:25][CH2:24][CH:22]([CH2:21][O:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[O:23][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]/[CH:48]=[CH:47]\[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:28][CH2:26][CH3:29])[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]/[CH:51]=[CH:50]\[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH3:42]

Komponenten

5

Edukt 3

HCID 28828273-Trityloxypropane-1,2-diolHCID 11258749Oleyl p-toluenesulfonateHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 702527781,2-O-dioleyl-3-O-tritylglycerolAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel2×

Versuchsvorschrift

In 120 ml of xylene was dissolved 3.22 g (10 mmol) of 1-O-tritylglycerol, followed by addition of 3.36 g (30 mmol) of t-butoxypotassium under argon. After 5 minutes of stirring, 30 ml of a solution of 12.8 g (30 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, then, at 50 for 1 hour. The reaction mixture was then 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/n-hexane-ethyl acetate) to provide 6.10 g (73%) of 1,2-O-dioleyl-3-O-tritylglycerol.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-242d2b09fce7499fb34d157358eee10c
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020317

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