Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1-Iodopropane | HCID 33643 | — |
| Reactant | HCID 86634965 | HCID 86634965 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86634967 | HCID 86634967 | 82.8% |
Reaction Steps
Under nitrogen atmosphere, to a mixture of 0.58 g of t-butyl (1R)-trans-3-[(E)-3-hydroxyimino-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylate, 2.0 g of 1-iodopropane and 10 ml of anhydrous dimethylformamide (hereinafter, abbreviated as DMF) was added 0.10 g of sodium hydroxide (60% dispersion in mineral oil) and the mixture was stirred at room temperature overnight. Thereafter, 1 mol/L hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then, filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.56 g of t-butyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-propoxyimino-1-propenyl]cyclopropanecarboxylate:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08039499B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-e1937e9649fb48b78ca002ff220d72cf |
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| Source note | uspto-grants-2011_10 |
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