HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → 4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-chloro-3-fluoropyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | (2-Chloro-3-Fluoropyridin-4-Yl)Methanol | HCID 54759140 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-chloro-3-fluoropyridine | HCID 59139177 | 93.3% |
Reaction Steps
A mixture of (2-chloro-3-fluoropyridin-4-yl)-methanol (200 mg, 1.24 mmol), imidazole (253 mg, 3.72 mmol) and tert-butyldimethylchlorosilane (373 mg, 2.48 mmol) in DMF was stirred at room temperature for 2 hours. Methylene chloride was then added to the reaction solution, and the solution was washed with saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel column chromatography to yield the title compound (319 mg, 93%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07897792B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-1b9d436e77bd43d8b440138b6b986d7b |
| Source note | uspto-grants-2011_03 |