Diethyl Oxalate → Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

HRID 1693352

反応式

HRID 1693352 の反応式
[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]>C(OCC)C.C(O)C>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])[CH3:14]

参加物

6

反応物 3

HCID 7268Diethyl OxalateHCID 5218284-Methyl-3-nitropyridineHCID 23670592Potassium ethoxide

生成物 1

HCID 23269548Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of potassium ethoxide (3.1 g, 36.2 mmol) in diethyl ether (70 mL) and ethanol (10 mL) under an argon atmosphere was added diethyl oxalate (4.9 mL, 36.2 mmol) and the reaction stirred at rt for 30 min. A solution of 4-methyl-3-nitropyridine (5.0 g, 36.2 mmol) in diethyl ether (20 mL) was added resulting in the immediate formation of a dark red precipitate. The reaction mixture was stirred at rt for 72 h, then cooled to 0° C. and filtered. The solid was dissolved in water (500 mL) acidified to pH 4 with acetic acid and the precipitate collected and dried to give the title compound as a red solid. δH (d6 DMSO): 1.27 (3H, t), 4.25 (2H, q), 6.74 (1H, s), 8.34 (1H, d), 8.43 (1H, d), 8.98 (1H, s); m/z (ES+)=239 [M+H]+.

後処理

  1. customresulting in the immediate formation of a dark red precipitate
  2. stirringThe reaction mixture was stirred at rt for 72 h
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in water (500 mL)
  6. customthe precipitate collected
  7. customdried

出典と根拠

ORDレコード
ord-478fe2ca9e2e42b381fc2503cdd81988
出典データセット
uspto-grants-2012_04
特許番号
US08158622B2

関連ノート

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