Methyl Acrylate → HCID 67703744, compound

HRID 55280Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:24])[CH2:10][CH2:11][CH2:12][C:13]([C:15]1[N:20]=[C:19](I)[C:18]([O:22][CH3:23])=[CH:17][CH:16]=1)=[O:14].[CH3:25][O:26][C:27](=[O:30])[CH:28]=[CH2:29]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:7][O:8][C:9](=[O:24])[CH2:10][CH2:11][CH2:12][C:13]([C:15]1[N:20]=[C:19](/[CH:29]=[CH:28]/[C:27]([O:26][CH3:25])=[O:30])[C:18]([O:22][CH3:23])=[CH:17][CH:16]=1)=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

244 mg of palladium acetate, 3.66 g of potassium carbonate and 3.4 g of tetrabutylammonium bromide are added to a solution of 3.87 g of 5-(2-iodo-3-methoxy-6-pyridyl)-5-oxopentanoic acid methyl ester and 1.87 ml of acrylic acid methyl ester in 10 ml of dimethylformamide, and the suspension is heated to 100° C. with stirring and under argon atmosphere for 5 hours. The solvent is removed in a vacuum, the residue is mixed with water, shaken out with ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. The crude product is chromatographed on silica gel with hexane/0-15% ethyl acetate. 1.89 g of 5-{3-methoxy-2-[2-methoxycarbonyl-(1E)-1-ethenyl-]-6-pyridyl}-5-oxopentanoic acid methyl ester of melting point 87°-89° C. is obtained.

Workup

customThe solvent is removed in a vacuum
additionthe residue is mixed with water
stirringshaken out with ethyl acetate
customthe organic phase is dried on sodium sulfate
concentrationconcentrated by evaporation
customThe crude product is chromatographed on silica gel with hexane/0-15% ethyl acetate

Sources & evidence

ORD record: ord-3391a5c3d2c241a6b0c93e0cf367357e
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624943

Reaction notes

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