HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoromethanesulfonic anhydride → 6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl Trifluoromethanesulfonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol | HCID 22018385 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | 6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl Trifluoromethanesulfonate | HCID 22285055 | — |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
Trifluoromethanesulfonic anhydride (9.1 mL) was added dropwise to a solution of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol (27.0 g) in pyridine (200 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C., diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate=1:1). Crystallization from diisopropyl ether gave the titled compound (29.6 g) as a colorless powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06649643B1 |
| Source dataset | uspto-grants-2003_11 |
| ORD ID | ord-572bb105840e4666833adeae9b41221f |
| Source note | uspto-grants-2003_11 |