HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 8-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 6-Bromo-8-ethyl-2,2,4,4-tetramethyl chroman | HCID 69548531 | — |
| 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 | 8-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman | HCID 69548613 | — |
Reaction Steps
Following general procedure D and using 6-bromo-8-ethyl-2,2,4,4-tetramethyl chroman (Intermediate 46, 0.5 g, 1.61 mmol), (trimethylsilyl)acetylene (1.57 g, 16.1 mmol), triethyl amine (8 mL), anhydrous tetrahydrofuran (10 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 5 g, 0.11 mmol), followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.137 g, 27%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06380256B1 |
| Source dataset | uspto-grants-2002_04 |
| ORD ID | ord-2ab02ea385a84edfa4f0c9382b3a6edf |
| Source note | uspto-grants-2002_04 |