Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Tetronic acid | HCID 521261 | — |
| Edukt | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Edukt | 9-(4-Chlorophenoxy)nonanoic acid | HCID 22902792 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Ethylacetate methanol | HCID 21584119 | — |
| Produkt | HCID 178418574 | HCID 178418574 | 30% |
Reaktionsschritte
To a stirring solution of 736 mg (7.36 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.2 mL (8.09 mmol) of triethylamine and 300 mg of 4-dimethylaminopyridine at 0° C. Next, 1.7 g (8.86 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.6 g (8.06 mmol) of 9-(4-chlorophenoxy)nonanoic acid are added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0 N HCl and extracted with four 50 mL portions of ether. 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 800 mg (30%) of 3-[9-(4-chlorophenoxy)-1-oxononyl]4-hydroxy-2(5H)-furanone.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US05242945 |
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| Quelldatensatz | uspto-grants-1993_09 |
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| ORD ID | ord-fe7b1958be8d4b2ab72860d32d3007d3 |
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| Quellennotiz | uspto-grants-1993_09 |
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