関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Tetronic acid | HCID 521261 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 反応物 | Myristoleic Acid | HCID 5281119 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Ethylacetate methanol | HCID 21584119 | — |
| 生成物 | HCID 178418583 | HCID 178418583 | 82% |
反応手順
To a stirring solution of 111 mg (1.11 mmol) of tetronic acid in 5 mL of dimethylformamide is added 185 μL (1.33 mmol) of triethylamine and 100 mg of 4-dimethylaminopyridine at 0° C. Next, 303 mg (1.33 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 300 mg (1.33 mmol) of myristoleic acid are added and the reaction mixture is stirred 3 days at room temperature. The reaction is acidified with 1.0N HCl and extracted with four 100 mL portions of ethyl acetate. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material is obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 280 mg (82%) of 4-hydroxy-3-((Z)-1-oxo-9-tetradecenyl)-2(5H)-furanone.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US05242945 |
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| 出典データセット | uspto-grants-1993_09 |
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| ORD ID | ord-74d123cdf41747398dd804672189e4fd |
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| 出典メモ | uspto-grants-1993_09 |
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