HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 4-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1,3-Di-tert-butyl-5-ethynyl-2-methoxy-benzene | HCID 22568851 | — |
| Reactant | Methyl-2-fluoro-4-iodo-phenyl acetate | HCID 69548383 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 4-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl-acetic acid methyl ester | HCID 69548862 | 89% |
Reaction Steps
Following General Procedure F and using 1,3-di-tert-butyl-5-ethynyl-2-methoxy-benzene (Intermediate 169, 0.087 g, 0.33 mmol), methyl-2-fluoro-4-iodo phenyl acetate (Reagent H, 0.088 g, 0.30 mmol), triethyl amine (5 mL), anhydrous tetrahydrofuran (10 mL), copper(I)iodide (0.02 g, 0. 1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.06 g, 0.085 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent, the title compound (0. 122 g, 89%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06531599B2 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-37f349bb8a894dcc86c032a2e28325ac |
| Source note | uspto-grants-2003_03 |