Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Ethyl cyanoacetate | HCID 7764 | — |
| Edukt | 1,2-Dibromoethane | HCID 7839 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | Ethyl 1-cyanocyclopropanecarboxylate | HCID 380810 | 72% |
Reaktionsschritte
A suspension of cyano-acetic acid ethyl ester (11.3 g, 0.1 mol), 1,2-Dibromo-ethane, Na4(n-Bu)4Br and K2CO3 in DMF (100 mL) was heated to 80° C. overnight. The mixture was poured into water (600 mL) and extracted with EtOAc (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4, concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (petroleum ether: EtOAc=10:1˜5:1) to give 1-cyano-cyclopropanecarboxylic acid ethyl ester (10 g, yield: 72%). 1H NMR (CDCl3 400 MHz): δ4.21 (q, J=7.2 Hz, 2H), 1.65-1.61 (m, 2H), 1.58-1.55 (m, 2H), 1.28 (t, J=7.2 Hz, 3H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09102591B2 |
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| Quelldatensatz | uspto-grants-2015_08 |
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| ORD ID | ord-501787d574114debbb6ecb65bb37e02b |
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| Quellennotiz | uspto-grants-2015_08 |
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