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

HRID 467123

Reaction equation

HRID 467123 reaction equation
[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]

Participants

5

Reactant 4

HCID 702EthanolHCID 897342-Methoxyethyl acetoacetateHCID 27716443-EthynylbenzaldehydeHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl ester

Product 1

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

Procedure

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%).

Workup

  1. additionwere successively added
  2. customat room temperature
  3. customThe admixture was reacted
  4. temperatureunder reflux
  5. temperaturewith heating for 12 hours
  6. customthe reaction
  7. distillationthe reaction solution was distilled away under reduced pressure
  8. custompurified
  9. customto give 2.1 g of the chloroform (1 : 1) to chloroform]

Sources & evidence

ORD record
ord-d5704b7d097b4eca9c81603ae798a68b
Source dataset
uspto-grants-1992_10
Patent number
US05158963

Linked notes

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