HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Thiosulfate → 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol | HCID 66608995 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-one | HCID 66608433 | 94.7% |
Reaction Steps
Dess-Martin reagent (248 mg) was added to a mixture of 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol (210 mg), acetonitrile (2.1 mL) and DMSO (200 μL) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (198 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822699B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-e89717aac73e494fab49add6423a75a6 |
| Source note | uspto-grants-2014_09 |