HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Glycolate → HCID 70982233, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Glycolate | HCID 12184 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 5-Bromo-2-chloropyrimidine | HCID 606665 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 70982233 | HCID 70982233 | 61% |
Reaction Steps
To a solution of ethyl 2-hydroxyacetate (0.081 g, 0.775 mmol) in toluene (1.0 mL) was added NaH (60% in mineral oil, 0.037 g, 0.931 mmol) at room temperature. The mixture was stirred for 30 min and a solution of 5-bromo-2-chloropyrimidine (0.100 g, 0.517 mmol) in toluene (0.5 mL) was added. The reaction mixture was stirred at 60° C. for 16 h. The mixture was diluted with EtOAc and slowly quenched with water. The organic layer was separated, washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (82 mg, 61% yield) as a clear colorless oil. LCMS, [M+H]+=260.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09062028B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-1b1b0321264f4f20b693213dc0e2a689 |
| Source note | uspto-grants-2015_06 |