Ethyl Acetoacetate → Diethyl 4-[4-(1H-imidazol-1-yl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 2379416ノート

反応式

HRID 2379416 の反応式
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=O.[NH4+:23].[OH-:24]>C(O)C>[CH3:18][C:16]1[NH:23][C:16]([CH3:18])=[C:15]([C:14]([O:20][CH2:21][CH3:22])=[O:24])[CH:10]([C:9]2[CH:12]=[CH:13][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:7][CH:8]=2)[C:15]=1[C:14]([O:20][CH2:21][CH3:22])=[O:19]

参加物

5

反応物 3

HCID 8868Ethyl AcetoacetateHCID 14923Ammonium HydroxideHCID 7365304-(1H-imidazol-1-yl)benzaldehyde

生成物 1

HCID 10475789Diethyl 4-[4-(1H-imidazol-1-yl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate収率 65%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 17.2 g (0.1 mol) of 4-(1H-imidazol-1-yl)benzaldehyde, 26 g (0.2 mol) of ethyl acetoacetate and 5 ml of concentrated NH4OH in absolute ethanol (25 ml) was refluxed for 6 hours. The mixture was poured into 500 ml of ice-water and the aqueous solution was extracted with methylene chloride. The organic layers were put together, dried over CaCl2 and evaporated under vacuum. The crude product was recrystallized from Et2O, giving 25.7 g (65%) of 1,4-dihydro-2,6-dimethyl-4-[4-(1H-imidazol-1-yl)phenyl]-3,5-pyridinedicarboxylic acid, diethyl ester, m.p. 231°-233° C.

後処理

  1. temperaturewas refluxed for 6 hours
  2. extractionthe aqueous solution was extracted with methylene chloride
  3. dry with materialdried over CaCl2
  4. customevaporated under vacuum
  5. customThe crude product was recrystallized from Et2O

出典と根拠

ORDレコード
ord-30c38d9714954b91b75fb3cf10a5e076
出典データセット
uspto-grants-1994_11
特許番号
US05362729

反応ノート

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