Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Hexafluoroacetone | HCID 12695 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Palladium barium sulphate | HCID 17887766 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Benzopyran | HCID 9211 | — |
Reaction Steps
According to Tetrahedron Letters, 1993, 34, 1815-1818, a compound (IIf) and trimethylsilyl acetylene are subjected to cross-coupling reaction in the presence of copper(I) iodide and tetrakis(triphenylphosphine)palladium and the resulting trimethylsilyl acetylene compound is treated with potassium carbonate in methanol to give a compound represented by the formula (XIX) set forth below. This compound is reacted with hexafluoroacetone using n-butyllithium to give a compound represented by the formula (XX). This compound is reduced with a palladium-barium sulfate catalyst under a hydrogen atmosphere to give a compound represented by the formula (XXI). This compound is reacted with sodium hydride to give a benzopyran derivative represented by the formula (XXII).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06455708B1 |
|---|
| Source dataset | uspto-grants-2002_09 |
|---|
| ORD ID | ord-ea37e5f848e64a47b6e407f1756ff9df |
|---|
| Source note | uspto-grants-2002_09 |
|---|
