HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 4-Iodophenylacetate → Methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 4-Iodophenylacetate | HCID 10378700 | — |
| Reactant | 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one | HCID 22568823 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate | HCID 12971710 | 75.2% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06603019B2 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-5cca1298f1b74be7a8b1109506d1986b |
| Source note | uspto-grants-2003_08 |