tert-Butyldimethylsilyl chloride → 1-O-benzyl-3-O-t-butyldimethylsilylglycerol

HRID 854714Notes

Reaction equation

HRID 854714 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 156217871-O-benzyl-3-O-t-butyldimethylsilylglycerolYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-552ddca8808c45cd84b7b28f7074aba4
Source dataset
uspto-grants-2007_08
Patent number
US07259273B1

Reaction notes

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