Ethanol → 5-Isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-3-methoxyethoxycarbonyl-4-(3-ethynylphenyl)pyridine

반응식

[C:1]([C:3]1[CH:4]=C([CH:8]=[CH:9][CH:10]=1)C=O)#[CH:2].[NH2:11]/[C:12](/[CH3:20])=[CH:13]\[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15].[C:21]([O:27][CH2:28][CH2:29][O:30][CH3:31])(=[O:26])[CH2:22][C:23]([CH3:25])=O.[CH2:32](O)[CH3:33]>>[CH:17]([O:16][C:14]([C:13]1[CH:23]([C:25]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[CH:2])[CH:4]=2)[C:22]([C:21]([O:27][CH2:28][CH2:29][O:30][CH3:31])=[O:26])=[C:32]([CH3:33])[NH:11][C:12]=1[CH3:20])=[O:15])([CH3:19])[CH3:18]

참가 물질

반응물 4

HCID 702Ethanol

HCID 897342-Methoxyethyl acetoacetate

HCID 27716443-Ethynylbenzaldehyde

HCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl ester

생성물 1

HCID 198134195-Isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-3-methoxyethoxycarbonyl-4-(3-ethynylphenyl)pyridine수율 53%

실험 절차

In 30 ml of dry ethyl alcohol was dissolved 1.3 g (10 mmol) of 3-ethynylbenzaldehyde, and 1.43 g (10 mmol) of isopropyl 3-aminocrotonate and 1.6 g (10 mmol) of methoxyethyl acetoacetate were successively added thereto at room temperature. The admixture was reacted under reflux with heating for 12 hours. After completing the reaction, the reaction solution was distilled away under reduced pressure and purified by subjecting to silica gel column chromatography [eluent: n-hexane-chloroform (1 : 1) to chloroform]to give 2.1 g of the chloroform (1 : 1) to chloroform] to give 2.1 g of the desired compound (yield: 53%).