1-o-Benzyl-3-o-t-butyldimethylsilyl-2-o-methyl-rac-glycerol → 1-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

HRID 843568Notes

Reaction equation

HRID 843568 reaction equation
C([O:8][CH2:9][CH:10]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[O:11][CH3:12])C1C=CC=CC=1>[Pd].CO>[Si:15]([O:14][CH2:13][CH:10]([CH2:9][OH:8])[O:11][CH3:12])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

4

Reactant 1

HCID 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 14 (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 h, 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 (15) (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-ba8d1dc08c7a47bf9954b20e010e118c
Source dataset
uspto-grants-2002_04
Patent number
US06380177B1

Reaction notes

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