HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 4-(8-Cycloproply-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)-benzoic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 4-iodobenzoate | HCID 142891 | — |
| Reactant | 8-Cyclopropyl-6-ethynyl-2,2,4,4-tetramethylchroman | HCID 22569006 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(8-Cycloproply-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)-benzoic acid ethyl ester | HCID 69548071 | — |
Reaction Steps
Following general procedure F and using 8-cyclopropyl-6-ethynyl-2,2,4,4-tetramethylchroman (Intermediate 34, 0.1 g, 0.38 mmol), ethyl-4-iodo-benzoate (Reagent A, 0.1 g, 0.34 mmol), triethyl amine (5 mL), tetrahydrofuran (10 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.11 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.135 g, 89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06603019B2 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-05cb41aa5c794298b533a4c394d85650 |
| Source note | uspto-grants-2003_08 |