HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium vinyltrifluoroborate → 4-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium vinyltrifluoroborate | HCID 23679353 | — |
| Reactant | 5-Bromo-4-cyclopropyl-1(3H)-isobenzofuranone | HCID 66643940 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 4-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one | HCID 66643947 | — |
Reaction Steps
A mixture of 5-bromo-4-cyclopropyl-2-benzofuran-1(3H)-one (760 mg, 3.004 mmol), potassium vinyltrifluoroborate (805 mg, 6.008 mmol) and Pd(dppf)Cl2 (100 mg) in 20 mL of TEA and 20 mL of EtOH was heated to reflux under N2 for 8 hours. When TLC showed complete reaction most of the solvent was removed, and the residue was dissolved in EtOAc (100 mL). The solution was washed with 0.1 N HCl, sodium bicarbonate, and brine, dried over sodium sulfate, filtered and concentrated. The resulting oil was purified by column chromatography to give 4-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018211B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-a7eb592f04594486b5033f638ffd782e |
| Source note | uspto-grants-2015_04 |