HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → (RS)-3-(2-propenyl)-3-cyclopenten-1-yl (1R)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | (1R,3S)-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride | HCID 6454308 | — |
| Reactant | (RS)-3-allyl-3-cyclopenten-1-ol | HCID 53659626 | — |
| Catalyst | 2,6-Di-tert-butyl-4-methylphenol | HCID 31404 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (RS)-3-(2-propenyl)-3-cyclopenten-1-yl (1R)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate | HCID 54417765 | 57.8% |
Reaction Steps
To a mixture of (RS)-3-(2-propenyl)-3-cyclopenten-1-ol (100 mg), 2,6-di-tert-butyl-4-methylphenol (5 mg), pyridine (82 mg) and toluene (5 ml), (1R)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl chloride (181 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 145 mg of (RS)-3-(2-propenyl)-3-cyclopenten-1-yl (1R)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (Compound No. 29). Yield 57% nD25 1.5100
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05925676 |
| Source dataset | uspto-grants-1999_07 |
| ORD ID | ord-39001ee5138e49b9812e529fe8ebc4d4 |
| Source note | uspto-grants-1999_07 |