Acetic Acid → Dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate

HRID 854032

反応式

HRID 854032 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.[C:14]([O:21][CH3:22])(=[O:20])[CH2:15][C:16]([O:18][CH3:19])=[O:17].N1CCCCC1.C(O)(=O)C>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:15]([C:14]([O:21][CH3:22])=[O:20])[C:16]([O:18][CH3:19])=[O:17])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 7943Dimethyl malonateHCID 8082PiperidineHCID 3576914-Methoxy-2-nitrobenzaldehyde

生成物 1

HCID 54325413Dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate収率 72%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 4-methoxy-2-nitrobenzaldehyde (21.3 g, Org. Synth., Vol. V, p-139, 1973), dimethyl malonate (16.5 g), piperidine (2.5 ml), and acetic acid (0.25 ml) in methanol (125 ml) was heated under reflux for 24 hr. The reaction mixture was concentrated, diluted with 1 N aqueous hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane=1:2) to obtain the titled compound (25 g).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hr
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with 1 N aqueous hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane=1:2)

出典と根拠

ORDレコード
ord-7d47fd831cff477c9378c9ecd6969386
出典データセット
uspto-grants-2007_08
特許番号
US07256204B2

関連ノート

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