HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Tetrahydrofuran → [2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-ylethynyl)phenyl]acetic acid ethyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Tetrahydrofuran | HCID 8028 | — |
| Edukt | Ethyl Acetate | HCID 8857 | — |
| Edukt | Ethyl 2-fluoro-4-iodophenylacetate | HCID 18740710 | — |
| Edukt | 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one | HCID 22568823 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Katalysator | HCID 178418476 | HCID 178418476 | — |
| Lösungsmittel | Hexane | HCID 8058 | — |
| Produkt | [2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-ylethynyl)phenyl]acetic acid ethyl ester | HCID 69548870 | — |
Reaktionsschritte
Following general procedure F and using 6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydro-naphthalene-1-one (Intermediate 13, 0.298 g, 1.43 mmol), 2-fluoro-4-iodo phenyl acetic acid ethyl ester (Reagent C, 0.44 g, 1.43 mmol), triethyl amine (Intermediate 13, 3 mL), anhydrous tetrahydrofuran (7 mL), copper(I)iodide (0.04 g, 0.2 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.15 g, 0.213 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 14-16% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.43 g, 77%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06303785B1 |
| Quelldatensatz | uspto-grants-2001_10 |
| ORD ID | ord-f330550c495e437aae497a3bb465491d |
| Quellennotiz | uspto-grants-2001_10 |