Glycerol → 1-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

HRID 496996Notes

Reaction equation

HRID 496996 reaction equation
OCC(CO)O.C([O:14][CH2:15][CH:16]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[O:17][CH3:18])C1C=CC=CC=1>[Pd].CO>[Si:21]([O:20][CH2:19][CH:16]([CH2:15][OH:14])[O:17][CH3:18])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 753GlycerolHCID 223164691-o-Benzyl-3-o-t-butyldimethylsilyl-2-o-methyl-rac-glycerol

Product 1

HCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the protected glycerol derivative Compound 41 (5.0 g, 16 mmol) and 10% palladium on activated carbon (wet Degussa type E101 NE/W) (0.43 g) in MeOH (50 mL) was evacuated using an aspirator pump and filled with hydrogen. After 2 hours, TLC analysis showed the reaction to be complete, the mixture was filtered through Celite and the filtrate was evaporated to dryness to give 1-O-t-butyldimethylsilyl-2-O-methyl-rac-glycerol (Compound 42) (99%) as a colourless oil.

Workup

  1. customwas evacuated
  2. additionfilled with hydrogen
  3. customthe reaction
  4. filtrationthe mixture was filtered through Celite
  5. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-76c83f38ce174f678d2651e9e1c74787
Source dataset
uspto-grants-2005_09
Patent number
US06949529B2

Reaction notes

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