HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
p-Toluenesulfonic acid → Ethyl 3-(N,N-dimethylamino)acrylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | p-Toluenesulfonic acid | HCID 6101 | — |
| Edukt | Ethyl 4,4,4-trifluoroacetoacetate | HCID 67793 | — |
| Edukt | Dimethylformamide dimethyl acetal | HCID 78373 | — |
| Edukt | Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester | HCID 53979199 | — |
| Produkt | Ethyl 3-(N,N-dimethylamino)acrylate | HCID 121015 | 75% |
Reaktionsschritte
My result is especially surprising in view of the results reported by Beck et al., vide supra, who attempted to prepare (2) by reacting ethyl trifluoroacetoacetate with DMF dimethyl acetal in the presence of a catalytic quantity of p-toluenesulfonic acid. The reaction resulted in the formation of ethyl 3-(N,N-dimethylamino)-2-propenoate (4) in 75% yield. Presumably, the methanol by-product further reacted with the target compound (2) to give the unexpected product and methyl trifluoroacetate.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06207828B1 |
| Quelldatensatz | uspto-grants-2001_03 |
| ORD ID | ord-d9087534728c4894a67931609e177ef0 |
| Quellennotiz | uspto-grants-2001_03 |