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

HRID 497004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497004
[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 Compound 42 (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 (Compound 43) (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-943678860afb41fd8b65cb62ff84dcb0
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949528B1

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