Pyridine → 1-o-t-Butyldimethylsilyl-2-o-methyl-3-o-oleoyl-rac-glycerol

HRID 843569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 843569
[Si:1]([O:8][CH2:9][CH:10]([CH2:13][OH:14])[O:11][CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15](Cl)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].N1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[O:11][CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 5364783Oleoyl chlorideHCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

Produkt 1

HCID 877595431-o-t-Butyldimethylsilyl-2-o-methyl-3-o-oleoyl-rac-glycerolAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of alcohol 15 (1.1 g, 5.0 mmol) in CH2Cl2 (10 mL) was added oleoyl chloride (1.8 mL, 5.5 mmol) followed, after 5 min, by the addition of pyridine (0.44 mL, 5.5 mmol). After TLC analysis indicated that the reaction had gone to completion, the mixture was partitioned between ethyl acetate (100 mL) and H2O (30 mL), the organic extract was dried (MgSO4) and concentrated to give 1-O-t-butyldimethylsilyl-2-O-methyl-3-O-oleoyl-rac-glycerol (16) (2.4 g, 99%) as a dark brown oil.

Aufarbeitung

  1. customthe mixture was partitioned between ethyl acetate (100 mL) and H2O (30 mL)
  2. extractionthe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-29690b9f588348f9bcabca01aec8809a
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380177B1

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