Participants
| Role | Name | HCID | Charge |
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| Reactant | Pyridine | HCID 1049 | — |
| Reactant | (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chloride | HCID 26620 | — |
| Reactant | 4-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol | HCID 11172116 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Dimefluthrin | HCID 213011 | 80% |
Reaction Steps
0.50 Gram of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride {containing the stereoisomers in a ratio of (1R)-trans form: (1R)-cis form: (1S)-trans form: (1S)-cis form =32.5:17.5:32.5:17.5} was added to a mixture of 0.55 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.23 g of pyridine and 7 ml of tetrahydrofuran under ice-cooling. The resulting mixture was heated to room temperature and stirred at room temperature for 8 hours. The reaction mixture was poured into about 20 ml of ice water and extracted twice with 40 ml of ethyl acetate. The combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.74 g (yield: 80%) of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present compound 2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06294576B1 |
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| Source dataset | uspto-grants-2001_09 |
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| ORD ID | ord-0b83c81c934e454b91eb89f5553c1cda |
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| Source note | uspto-grants-2001_09 |
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