tert-Butyldimethylsilyl chloride → HCID 15621787, Verbindung

HRID 496994

Reaktionsgleichung

Reaktionsgleichung von HRID 496994
[C:1]([O:20][CH2:21][CH:22]([CH2:25][OH:26])[O:23]C)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]C/C=C\CCCCCCCC.C(OCC(CO)O)C1C=CC=CC=1.[Si:40](Cl)([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:20][CH2:21][CH:22]([CH2:25][O:26][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[OH:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 980723-(Benzyloxy)-1,2-propanediolHCID 99475821-o-Oleoyl-2-o-methyl-rac-glycerol2×

Produkt 1

HCID 15621787HCID 15621787, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-O-Oleoyl-2-O-methyl-rac-glycerol (Compound 44) To a mixture of 1-O-benzyl-glycerol (27 mL, 0.16 mol) and t-butyldimethylsilyl chloride (25 g, 0.17 mol) in dry CH2Cl2 (250 mL) under N2 was added DMAP (0.8 g, 6.6 mmol) followed by the addition of TEA (23 mL, 0.17 mol). After 3 hours, the mixture was washed with H2O (2×100 mL), dried (MgSO4) and concentrated to give 1-O-benzyl-3-O-t-butyldimethylsilyl-rac-glycerol (40) (48.8 g, 100%) as a yellow oil.

Aufarbeitung

  1. washthe mixture was washed with H2O (2×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a32c6aa5f7274fb5a1c2d219d444d7fe
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949529B2

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