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Ethyl Acetate → Prop-2-yn-1-yl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | 2-[4-(Diethylamino)-2-hydroxybenzoyl]benzoic acid | HCID 79878 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | Prop-2-yn-1-yl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate | HCID 58675397 | — |
反応手順
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).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07906108B2 |
| 出典データセット | uspto-grants-2011_03 |
| ORD ID | ord-f5ffeee3a54c4665b59b0d4fa996760b |
| 出典メモ | uspto-grants-2011_03 |