HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 58520617, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Methyl-5-hydroxypyridine | HCID 14275 | — |
| Reactant | Bromomethylcyclopropane | HCID 81503 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58520617 | HCID 58520617 | 52% |
Reaction Steps
To a solution of 6-methylpyridin-3-ol (5.0 g, 46 mmol) in DMF (45 mL) were added cesium carbonate (16.5 g, 53 mmol) and (bromomethyl)cyclopropane (7.1 g, 53 mmol) at room temperature. After being stirred at room temperature for 18 hours, the mixture was poured into H2O, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1 (v/v)) to give 3.9 g (52% yield) of the title compound as a yellow oil:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09101616B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-643c4c32de0c4749881b1d0b8f1a1bc6 |
| Source note | uspto-grants-2015_08 |