Diethyl Malonate → Diethyl 2-(3-methyl-2-nitrobenzylidene)malonate

HRID 1435937ノート

反応式

HRID 1435937 の反応式
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([O:21][CH2:22][CH3:23])=[O:20]

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 516892Sodium BicarbonateHCID 135735673-Methyl-2-nitrobenzaldehyde

生成物 1

HCID 68898055Diethyl 2-(3-methyl-2-nitrobenzylidene)malonate収率 90.8%

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

反応条件

温度
100 °C

実験手順

To a solution of this aldehyde (10.0 g, 60.6 mmol) in 20 mL of acetic anhydride was added diethyl malonate (9.7 g, 60.6 mmol) and sodium bicarbonate (7.6 g, 91 mmol). The reaction mixture was stirred at 100° C. for 24 h. The reaction was allowed to cool and then was partitioned between ethyl acetate and water. The organics were washed sequentially with water, aq sat'd NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 16.9 g (90%) of the title compound.

後処理

  1. temperatureto cool
  2. customwas partitioned between ethyl acetate and water
  3. washThe organics were washed sequentially with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-5ad771bd5b564352bf233dcaab2d6fed
出典データセット
uspto-grants-2009_11
特許番号
US07618980B2

反応ノート

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