Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Methylpyridine | HCID 7963 | — |
| Reactant | Ethyl 5-chlorothiophene-2-carboxylate | HCID 521808 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 65583291 | HCID 65583291 | 37.8% |
Reaction Steps
To a solution of 4-methylpyridine (32.3 mmol) and ethyl 5-chlorothiophene-2-carboxylate (35.5 mmol) in anhydrous THF (58 mL) at 0° C., under N2 was added dropwise a solution of lithium bis(trimethylsilyl)amide (1 molar solution in hexanes, 64.5 mmol). The mixture was stirred 3 h at 5° C. The resulting precipitate was filtered and acidified with 6 molar HCl. The precipitate was then filtered and dried to afford 2.9 g (35% yield) of 1-(5-chloro-2-thienyl)-2-(pyridin-4-yl)ethanone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08685974B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-9d27d3d7ebbd4a48a4c9151639a07a24 |
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| Source note | uspto-grants-2014_04 |
|---|