HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropanol → 5-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | Isopropyl acetoacetate | HCID 68329 | — |
| Reactant | 2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- | HCID 643756 | — |
| Reactant | 3-Ethynylbenzaldehyde | HCID 2771644 | — |
| Catalyst | Piperidine | HCID 8082 | — |
| Product | 5-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridine | HCID 19813405 | 58.6% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05158963 |
| Source dataset | uspto-grants-1992_10 |
| ORD ID | ord-d00579241cd841498e28cdd9874272dc |
| Source note | uspto-grants-1992_10 |