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Methyl Acrylate → 3-(6-formyl-3-methoxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester

HRID 55286
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인쇄 미리보기

반응식

HRID 55286 반응식
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
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참가 물질

7

반응물 3

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

생성물 1

HCID 867507673-(6-formyl-3-methoxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845
palladium(II) acetate
촉매
HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-341d47c9f25a41fbbd585b6cf73115be
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05624943

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