Methyl Acrylate → HCID 86750767, compound

HRID 55286Notes

Reaction equation

HRID 55286 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH:10]=[O:11])[N:3]=1.[CH3:12][O:13][C:14](=[O:17])[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][O:13][C:14](=[O:17])/[CH:15]=[CH:16]/[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH:10]=[O:11])[N:3]=1

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 199574546-Iodo-5-methoxypicolinaldehyde

Product 1

HCID 86750767HCID 86750767, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Under the conditions of example 16 H, a solution of 20 g of 2-iodo-3-methoxypyridine-6-aldehyde in 100 ml of dimethylformamide is reacted with 33.5 ml of acrylic acid methyl ester in the presence of 1.73 g of palladium acetate, 26.1 g of potassium carbonate and 23.8 g of tetrabutylammonium bromide, worked up, and the crude product is chromatographed on silica gel with hexane/0-50% ethyl acetate. 11.66 g of 3-(6-formyl-3-methoxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester of melting point 132°-134° C. is obtained.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-50% ethyl acetate

Sources & evidence

ORD record
ord-341d47c9f25a41fbbd585b6cf73115be
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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