Butyl (2E)-3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-2-propenoate → Butyl 3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]propanoate

HRID 15349

Reaction equation

HRID 15349 reaction equation
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])[CH:9]=1)([CH3:4])[CH3:3].[H][H]>[Pd].CO>[CH3:3][C:2]([Si:5]([CH3:25])([CH3:26])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])[CH:9]=1)([CH3:1])[CH3:4]

Participants

5

Reactant 2

HCID 57486889Butyl (2E)-3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-2-propenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 57486890Butyl 3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]propanoateYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of butyl (2E)-3-[4-({[(1,1 dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-2-propenoate (4.84 g, 12.49 mmol) and 10% palladium on carbon in methanol (200 ml) was stirred at rt over one atmosphere of hydrogen for 3 h. The mixture was filtered through Celite and evaporated to give the desired product (4.76 g, 98%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-fe81060b0fbe43af8449815bb57ad0f4
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Linked notes

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