HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Methyl 4-Iodophenylacetate → Methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Methyl 4-Iodophenylacetate | HCID 10378700 | — |
| 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 | Triethylamine | HCID 8471 | — |
| Produkt | Methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate | HCID 12971710 | 75,2% |
Reaktionsschritte
Using General Procedure F; 6-ethynyl-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 13, 190.0 mg, 0.96 mmol) and methyl-4-iodophenyl)-acetate (Reagent B, 245.0 mg, 0.96 mmol) in triethyl amine (8 mL) was treated with copper(I)iodide (46 mg, 0.24 mmol) and sparged with argon for 15 minutes. Dichlorobis(triphenylphosphine)palladium(II) (168 mg, 0.24 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (10-20% EtOAc—hexanes) afforded 250.0 mg (75%) of the title compound as a pale-yellow solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06855512B2 |
| Quelldatensatz | uspto-grants-2005_02 |
| ORD ID | ord-01ec60cbc0e14b8ea2af3556f1d3d188 |
| Quellennotiz | uspto-grants-2005_02 |