3-Nitrobenzaldehyde → 2-Ethoxyethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

HRID 894660ノート

反応式

HRID 894660 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])=[O:17])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 814132-Ethoxyethyl acetoacetate

生成物 1

HCID 545745632-Ethoxyethyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 3-nitrobenzaldehyde (4.54 g), 2-ethoxyethyl acetoacetate (5.23 g) and piperidine (85.2 mg) in benzene (15 ml) was refluxed under azeotropic dehydration for 3 hours. The resultant mixture was washed with water, an aqueous solution saturated with sodium chloride and water in turn, dried and concentrated to give an oil of 2-ethoxyethyl 2-(3-nitrobenzylidene)acetoacetate. To this oily product was added ethyl 3-amino-4,4-diethoxycrotonate (6.5 g). The mixture was heated at 110° C. for about 3 hours. The reaction mixture was dissolved in ethyl acetate and washed with water twice and dried. The solvent was removed from the mixture to give an oil (15.58 g). This oil was subjected to column chromatography on silica gel with an eluent (a mixture of 10 parts of benzene and one part of ethyl acetate by volume) to give an oily substance (8.09 g). This oily substance (0.93 g) was treated with a mixture of n-hexane and diethyl ether to give crystals, which were further recrystallized from a mixture of n-hexane and diethyl ether to give yellow granules (565.2 mg) of 2-ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 99° to 100° C.

後処理

  1. temperaturewas refluxed under azeotropic dehydration for 3 hours
  2. washThe resultant mixture was washed with water
  3. dry with materialan aqueous solution saturated with sodium chloride and water in turn, dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-21dcb0d6aa634e1f81999f5f8a4acf6b
出典データセット
uspto-grants-1981_08
特許番号
US04284634

反応ノート

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