Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Bromocyclopropane | HCID 78037 | — |
| Reactant | Magnesium | HCID 5462224 | — |
| Reactant | N,N-diethyl-4-(3-methoxybenzoyl)benzamide | HCID 9995598 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22671451 | HCID 22671451 | 53% |
Reaction Steps
A solution of cyclopropyl bromide (0.31 ml) dissolved in tetrahydrofuran (1.5 ml) was added with magnesium (46.9 mg) and stirred at 60° C. for 1 hour to prepare a Grignard reagent. The Grignard reagent was added with a solution of 3-(4-diethylcarbamoylbenzoyl)anisole (150 mg) synthesized in accordance with the method described in WO97/10230, which was dissolved in tetrahydrofuran (1.5 ml), and then stirred at 60° C. for 2 hours. The reaction mixture was added with saturated aqueous ammonium chloride (4 ml) with ice cooling to terminate the reaction and then extracted twice with dichloromethane (4 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1→1:1) to obtain 90.9 mg of the title compound. Yield: 53%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06790854B2 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-d70df8e30e494bdfb0af6f44d1770d6a |
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| Source note | uspto-grants-2004_09 |
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