HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 1-Cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 4-iodobenzoate | HCID 142891 | — |
| Reactant | 4-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester | HCID 69548418 | — |
| 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 | 1-Cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline | HCID 22568871 | — |
Reaction Steps
Following general procedure F and using 1-cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydro quinoline (Intermediate 53, 0.11 g, 0.43 mmol), ethyl-4-iodo-benzoate (Reagent A, 0.11 g, 0.9 mmol), triethyl amine (3 mL), tetrahydrofuran(3 mL), copper(I)iodide (0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.060 g, 0.085 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 (0.05 g, 31%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06252090B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-3a8f26fc804b49ec84cb7bc22bfc1245 |
| Source note | uspto-grants-2001_06 |