Reaktion #941896

Reaktionsgleichung

1-O-Oleoyl-2-O-methyl-rac-glycerol

Compound 44

1-O-Oleoyl-2-O-methyl-rac-glycerol

1-O-benzyl-glycerol

t-butyldimethylsilyl chloride

→

1-O-benzyl-3-O-t-butyldimethylsilyl-rac-glycerol

Ausbeute 100.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe mixture was washed with H2O (2×100 mL)
2. 2
   Trocknendried (MgSO4)
3. 3
   Einengenconcentrated

Vorschrift

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. 1H NMR (360 MHz; CDCl3): (0.06 (6H, s, Me2Si), 0.89 (9H, s, ButSi), 3.48-3.56 (2H, m, 1-H2 or 3-H2), 3.64 (1H, dd, J 10 and 5.5 Hz, 1-H or 3-H), 3.68 (1H, dd, J 10 and 5 Hz, 1-H or 3-H), 3.86 (1H, quintet, J 5.5 Hz, 2-H), 4.56 (2H, s, —OCH2Ph) and 7.27-7.35 (5H, m, —Ph).

Quelle