HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Indole → 5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Indole | HCID 798 | — |
| Edukt | Flurothyl | HCID 9528 | — |
| Edukt | 3-Methyl-4-nitrophenol | HCID 17412 | — |
| Edukt | Sodium hydride | HCID 24758 | — |
| Edukt | Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate) | HCID 67942 | — |
| Edukt | Phenolate | HCID 119047 | — |
| Lösungsmittel | Hexamethylphosphoramide | HCID 12679 | — |
| Produkt | 5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid | HCID 57646517 | — |
Reaktionsschritte
5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid was prepared following the procedure reported in Synthesis (1980) 727. 3-methyl-4-nitrophenol (Aldrich) was deprotonated with sodium hydride in HMPA, and the resulting phenolate alkylated with 2,2,2-trifluoroethyl tosylate (Aldrich). The resulting trifluoroethyl ether was then converted to the indole using the Batcho-Leimgruber protocol. Formylation and oxidation as described herein gave the title compound as an off-white solid. MS (m/e) 260.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09434724B2 |
| Quelldatensatz | uspto-grants-2016_09 |
| ORD ID | ord-4d827cc537484e228c849fdeaddc49cf |
| Quellennotiz | uspto-grants-2016_09 |