HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chlorobenzoic Acid → 4-(Pyridin-2-yl)but-3-ynyl 2-chlorobenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chlorobenzoic Acid | HCID 8374 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-(Pyridin-2-yl)but-3-yn-1-ol | HCID 11008063 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(Pyridin-2-yl)but-3-ynyl 2-chlorobenzoate | HCID 66598524 | 43.3% |
Reaction Steps
To solution of 2-chlorobenzoic acid (330 mg, 2.10 mmol), 4-(pyridin-2-yl)but-3-yn-1-ol (310 mg, 2.1 mmol), in DCM (7 mL), was successively added EDCI.HCl (600 mg, 3.2 mmol) and DMAP (13 mg, 0.105 mmol). The resulting mixture was then stirred overnight at ambient temperature. The reaction mixture was concentrated. Purification over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt: 80/20 as eluent) to afford 260 mg of 4-(pyridin-2-yl)but-3-ynyl 2-chlorobenzoate (Yield: 43%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101637B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-62c008715859439694834aa96a4dac63 |
| Source note | uspto-grants-2012_01 |