HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Thiosulfate → 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynal
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol | HCID 66608834 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynal | HCID 86662976 | 75.9% |
Reaction Steps
Dess-Martin reagent (4.99 g) was added to a mixture of 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol (2.80 g) in acetonitrile (30 mL) 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 (2.11 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822699B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-bdd1574a795c4cae9676f1da1df80b97 |
| Source note | uspto-grants-2014_09 |