HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Chloride → 7-bromo-4-(1-ethoxyvinyl)-2H-chromen-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | Stannane, tributyl(1-ethoxyethenyl)- | HCID 619414 | — |
| Reactant | 7-bromo-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate | HCID 19426948 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 7-bromo-4-(1-ethoxyvinyl)-2H-chromen-2-one | HCID 23370204 | — |
Reaction Steps
To a solution of 7-bromo-4-trifluoromethanesulfonyloxycoumarin (5.1 g, 13.7 mmol) in dioxane is added tributyl(1-ethoxyvinyl)tin (4.8 mL, 14.2 mmol), (Ph3P)4Pd (0.790 g, 0.7 mmol) and LiCl (1.74 g, 41 mmol). The mixture is refluxed for 4 h, cooled and partitioned between aqueous NH4Cl and EtOAc. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic layers are washed with brine and dried over anhydrous Na2SO4. The solvent is evaporated and the residue is chromatographed on silica gel (CH2Cl2/EtOAc; 95:5) and triturated in hexane/Et2O to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07553973B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-87c3e03c5a54408cb285d11827932609 |
| Source note | uspto-grants-2009_06 |