HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 3,4-dimethyl-3-cyclopenten-1-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride | HCID 11334477 | — |
| Reactant | 3,4-Dimethyl-3-cyclopenten-1-ol | HCID 13507601 | — |
| Catalyst | 2,6-Di-tert-butyl-4-methylphenol | HCID 31404 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 3,4-dimethyl-3-cyclopenten-1-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate | HCID 86754274 | 86.5% |
Reaction Steps
To a mixture of 3,4-dimethyl-3-cyclopenten-1-ol (175 mg), 2,6-di-tert-butyl-4-methylphenol (5 mg), pyridine (150 mg) and toluene (10 ml), (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride (395 mg) was added under ice-cooling. The resulting reaction mixture was further allowed to react for 8 hours at room temperature. Then the reaction mixture was subjected to the same post-treatment as in Example 1 to afford 441 mg of 3,4-dimethyl-3-cyclopenten-1-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (Compound No. 3). Yield 84% nD25 1.4620
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05925676 |
| Source dataset | uspto-grants-1999_07 |
| ORD ID | ord-73b0a9d04d20408c8b1369f82b31868d |
| Source note | uspto-grants-1999_07 |