HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → Prop-2-yn-1-yl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-[4-(Diethylamino)-2-hydroxybenzoyl]benzoic acid | HCID 79878 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Prop-2-yn-1-yl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate | HCID 58675397 | — |
Reaction Steps
A solution of 200 mmol 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid, 500 mmol propargylic alcohol, 220 mmol 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), and 500 mmol N-ethyldiisopropylamine in 600 mL DMF is stirred at room temperature for 2 h. 1 L of ethyl acetate is added and the solution extracted with 1 L water. The organic layer is separated, dried (Na2SO4), and the solvent evaporated. The crude product is purified via FC (n-hexane/EtOAC 2:1) yielding 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid prop-2-ynyl ester. MS (EI): 374 (18%, M+Na+), 352 (100%, M+H+), 296 (17%). UV (EtOH): λmax=356 nm (ε=31'648).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07906108B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-f5ffeee3a54c4665b59b0d4fa996760b |
| Source note | uspto-grants-2011_03 |