Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Chloride | HCID 4873 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3,3-Diethoxy-1-propene | HCID 62477 | — |
| Reactant | 5-Bromophthalide | HCID 603144 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 89526051 | HCID 89526051 | — |
Reaction Steps
To a stirred solution of 5-Bromo-2-benzofuran-1(3H)-one (20 g, 94 mmol) in DMF (500 mL) was added Acrolein diethyl acetal (37 g, 282 mmol), Bu4NOAc (57 g, 188 mmol), K2CO3 (19.5 g, 141 mmol), KCl (7.0 g, 94 mmol) and Pd(OAc)2 (200 mg). The mixture was stirred for 2.5 hours at 90° C. After the mixture was cooled, 2 N HCl was slowly added and the resulting reaction mixture was stirred at room temperature for 10 min, and diluted with EtOAc, washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified with silica gel chromatography (petrol ether/EtOAc=2:1) to give title product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08999990B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-040b2cd78d0f43f0842ff90a42eea094 |
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| Source note | uspto-grants-2015_04 |
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