HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Alcohol → Methyl 2,3-dihydrobenzofuran-7-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2,3-Dihydro-1-benzofuran-7-carboxylic acid | HCID 2795014 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 2,3-dihydrobenzofuran-7-carboxylate | HCID 15062252 | 142.6% |
Reaction Steps
A solution of 0.2 g (1.22 mmol) of 7-dihydrobenzofuran carboxylic acid, 0.13 g (1.22 mmol) of benzyl alcohol, 0.3 g (2.44 mmol) of DMAP and 0.46 g (2.44 mmol) of 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride in 5 mL of CH2Cl2 was stirred at rt for 12 h. The reaction mixture was partitioned between CH2Cl2 and water and the pH was adjusted to pH=1 with 1N HCl solution. The reaction mixture was extracted with CH2Cl2 and the combined organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 6:1) to give 0.31 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06303593B1 |
| Source dataset | uspto-grants-2001_10 |
| ORD ID | ord-22f91d74bdc84ba6b1fc4c772e251f88 |
| Source note | uspto-grants-2001_10 |