Methyl Acrylate → (E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate

HRID 55258

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

5.2 g of palladium(II) acetate, 77.8 g of potassium carbonate and 72.5 g of tetrabutylammonium bromide are added to a solution of 70 g of 3-benzyloxy-2-iodopyridine and 39.8 ml of acrylic acid methyl ester in 120 ml of dimethylformamide, and the suspension is stirred under argon atmosphere for 10 hours at 100° C. (bath temperature). The reaction mixture is concentrated by evaporation in a vacuum, the residue is added to water and shaken out with ethyl acetate. The organic phase is washed three times with water and once with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation. The crude product is chromatographed on silica gel with hexane/10-25% ethyl acetate. 48.2 g of 3-(3-benzyloxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester is obtained as oil.

Workup

concentrationThe reaction mixture is concentrated by evaporation in a vacuum
additionthe residue is added to water
stirringshaken out with ethyl acetate
washThe organic phase is washed three times with water
dry with materialonce with saturated common salt solution, dried with sodium sulfate
concentrationconcentrated by evaporation
customThe crude product is chromatographed on silica gel with hexane/10-25% ethyl acetate

Sources & evidence

ORD record: ord-d4846378d04a4d3fb9385b65082d0c14
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624943

Linked notes

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