HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → HCID 18794886, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | HCID 18794915 | HCID 18794915 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18794886 | HCID 18794886 | 89.5% |
Reaction Steps
645 mg of (2RS,3SR)-3-(hydroxymethyl)-4-{5-(phenylcarbamoyl)-2-furyl}butan-2-ol in 12 ml of dimethylformamide was mixed with 305 mg of imidazole and 372 mg of tert-butyldimethylsilyl chloride under cooling with ice and stirred at the same temperature for 1 hour. Saturated aqueous ammonium chloride and ethyl acetate were added to the reaction solution for extraction, and the organic layer was washed with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1] to give 805 mg of the title compound as a colorless oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06048894 |
| Source dataset | uspto-grants-2000_04 |
| ORD ID | ord-0a3c75d3b14a4a86acda6d60b3d20211 |
| Source note | uspto-grants-2000_04 |