Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Trimethylsulfonium iodide | HCID 75127 | — |
| Reactant | HCID 18000926 | HCID 18000926 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18000846 | HCID 18000846 | 61.9% |
Reaction Steps
507 mg of sodium hydride (55% in paraffin oil) is introduced into 20 ml of dimethylformamide under nitrogen at 0° C., and 1.38 g of trimethylsulfonium iodide is added. After 30 minutes at this temperature, 1.06 g of ketone 52 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, 702 mg of title compound 53 is obtained as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06613920B1 |
|---|
| Source dataset | uspto-grants-2003_09 |
|---|
| ORD ID | ord-a84ad23f6bcc4394aa91e1be34821206 |
|---|
| Source note | uspto-grants-2003_09 |
|---|