Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | 6-Phenoxypyridine-2-carbaldehyde | HCID 12941006 | — |
| Reactant | rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride | HCID 44152741 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 86739863 | HCID 86739863 | 77% |
Reaction Steps
6.7 g (0.02 mol) of (±)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid-chloride, dissolved in 10 ml of n-hexane, were added dropwise to a mixture of 40 ml of n-hexane, 1.5 g of sodium cyanide, 2 ml of water, 3.98 g (0.02 mol) of 2-formyl-6-phenoxy-pyridine and 0.5 g of tetrabutylammonium bromide at 20° to 25° C., while stirring, and the mixture was then stirred for 4 hours at 20° to 25° C. 100 ml of toluene were then added to the reaction mixture, and the latter was extracted by shaking twice with 60 ml of water. The organic phase was separated off and dried over magnesium sulphate, and the solvent was distilled off in a water jet vacuum. The last solvent residues were removed by incipient distillation for a short time at a bath temperature of 60° C./1 mm Hg. 6.4 g (77 % of theory) of cyano-(6-phenoxy-2-pyridinyl)-methyl (±)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylate were obtained as a viscous yellow oil. The structure was established by the 1H-NMR spectrum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04491585 |
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| Source dataset | uspto-grants-1985_01 |
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| ORD ID | ord-4533f43dca4a4749b24540cfbee84d36 |
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| Source note | uspto-grants-1985_01 |
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