Methyl 4-tert-butyldimethylsilyloxy-3,5-di(2-propen-1-yl)benzoate → Methyl 4-tert-butyldimethylsilyloxy-3,5-dipropylbenzoate

HRID 5931Notes

Reaction equation

HRID 5931 reaction equation
[Si:1]([O:8][C:9]1[C:18]([CH2:19][CH:20]=[CH2:21])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:22][CH:23]=[CH2:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>C(O)C>[Si:1]([O:8][C:9]1[C:10]([CH2:22][CH2:23][CH3:24])=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][C:18]=1[CH2:19][CH2:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 19385712Methyl 4-tert-butyldimethylsilyloxy-3,5-di(2-propen-1-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 19385738Methyl 4-tert-butyldimethylsilyloxy-3,5-dipropylbenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.0 g (14.45 mmol) of the product of Step C in 250 mL ethanol containing 5% Rh/C (0.25 g) was shaken under a 40 psi pressure of hydrogen. Upon completion of reduction, the mixture was filtered through Celite, the filter cake was washed with methanol and dichloromethane. Removal of solvents afforded 4.55 g (90%) of the title compound.

Workup

  1. filtrationUpon completion of reduction, the mixture was filtered through Celite
  2. washthe filter cake was washed with methanol and dichloromethane
  3. customRemoval of solvents

Sources & evidence

ORD record
ord-1f275fee41654dd1ae6647f1d1d8064a
Source dataset
uspto-grants-1993_09
Patent number
US05246944

Reaction notes

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