tert-Butyldimethylsilyl chloride → HCID 15621787, compound

HRID 496994

Reaction equation

HRID 496994 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 15621787HCID 15621787, compoundYield 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.

Workup

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

Sources & evidence

ORD record
ord-a32c6aa5f7274fb5a1c2d219d444d7fe
Source dataset
uspto-grants-2005_09
Patent number
US06949529B2

Linked notes

Loading…