Isopropanol → 5-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridine

HRID 467127

反応式

HRID 467127 の反応式
[C:1]([C:3]1[CH:4]=C([CH:8]=[CH:9][CH:10]=1)C=O)#[CH:2].[C:11]([O:17][CH:18]([CH3:20])[CH3:19])(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH2:21]/[C:22](/[CH3:29])=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25].[CH:30](O)(C)[CH3:31]>N1CCCCC1>[CH2:27]([O:26][C:24]([C:23]1[CH:13]([C:15]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[CH:2])[CH:4]=2)[C:12]([C:11]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[C:30]([CH3:31])[NH:21][C:22]=1[CH3:29])=[O:25])[CH3:28]

参加物

6

反応物 4

HCID 3776IsopropanolHCID 68329Isopropyl acetoacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 27716443-Ethynylbenzaldehyde

生成物 1

HCID 198134055-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridine収率 58.6%

試薬・触媒・溶媒 1

HCID 8082Piperidine触媒

実験手順

To a mixture of 0.65 g (0.005 mol) of 3ethynylbenzaldehyde, 1.08 g (0.0075 mol) of isopropyl acetoacetate and 25 ml of isopropyl alcohol were added 2 to 3 drops of piperidine. After heating the mixture under reflux for 24 hours, 0.65 g (0.005 mol) of ethyl 3-aminocrotonate was added thereto, further the admixture was heated under reflux for 24 hours. After completing the reaction, the reaction mixture was concentrated. The obtained precipitate was purified by subjecting to silica gel column chromatography [eluent: n-hexane to n-hexane: ethyl acetate (7 : 3)] to give 1.1 g of the desired compound (yield: 58.6%).

後処理

  1. temperatureAfter heating the mixture
  2. temperatureunder reflux for 24 hours
  3. temperaturefurther the admixture was heated
  4. temperatureunder reflux for 24 hours
  5. customthe reaction
  6. concentrationthe reaction mixture was concentrated
  7. customThe obtained precipitate was purified

出典と根拠

ORDレコード
ord-d00579241cd841498e28cdd9874272dc
出典データセット
uspto-grants-1992_10
特許番号
US05158963

関連ノート

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