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

HRID 930871ノート

反応式

HRID 930871 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-de2d6aa03c4042f680d3eb0a7009f046
出典データセット
uspto-grants-2016_03
特許番号
US09296741B2

反応ノート

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