HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 1-[1-(4-Methylphenyl)cyclopropyl]ethan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Trimethylsulfonium iodide | HCID 75127 | — |
| Reactant | 3-(4-Methylphenyl)-3-buten-2-one | HCID 18000773 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-[1-(4-Methylphenyl)cyclopropyl]ethan-1-one | HCID 18000934 | 48.6% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
507 mg of sodium hydride (55% in paraffin oil) is introduced into 20 ml of dimethylformamide under nitrogen at 0° C., and 1.36 g of trimethylsulfonium iodide is added. After 30 minutes at this temperature, 845 mg of ketone 40 is added in drops to 4 ml of dimethylformamide. It is stirred for 1 more hour at 0° C., then quenched with sodium chloride solution, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. After chromatography on silica gel with ethyl acetate/hexane, 447 mg of title compound 41 is obtained as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06642218B2 |
| Source dataset | uspto-grants-2003_11 |
| ORD ID | ord-8146f50c552f4d80b5e742a9d737bd35 |
| Source note | uspto-grants-2003_11 |