Ethanol → (Z)-ethyl 3-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-2-hydroxyacrylate

HRID 930871노트

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HRID 930871 반응식
C(O)C.[Br:4][C:5]1[C:6]([CH3:16])=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([O:11][CH3:12])=[N:9][CH:10]=1.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].[O-]CC.[K+]>C(OCC)(=O)C.CCOCC>[Br:4][C:5]1[C:6](/[CH:16]=[C:17](\[OH:23])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([O:11][CH3:12])=[N:9][CH:10]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 23670592Potassium ethoxideHCID 407869095-Bromo-2-methoxy-3-nitro-4-picoline

생성물 1

HCID 136348377(Z)-ethyl 3-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-2-hydroxyacrylate수율 46%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

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온도
45 °C

실험 절차

To a solution of ethanol (15 mL) and ether (150 mL) were added 5-bromo-2-methoxy-4-methyl-3-nitropyridine (14.82 g, 60 mmol), diethyl oxalate (13.15 g, 90 mmol), and potassium ethoxide (6.06 g, 72 mmol). The reaction mixture was heated at 45° C. for 24 hours. During the reaction, the flask was shaken by hand several times. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 10-20% ethyl acetate in hexanes to 9.5 g of the title compound (yield 46%).

후처리

  1. customDuring the reaction
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted with additional ethyl acetate three times
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-de2d6aa03c4042f680d3eb0a7009f046
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296741B2

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