Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | 4-Iodophenol | HCID 10894 | — |
| Reactant | Tert-butyl 2-(benzamido)-4-vinylbenzoate | HCID 67343635 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 67342138 | HCID 67342138 | 64.9% |
Reaction Steps
0.12 g of 4-iodophenol, 0.18 mL of tributylamine and 4.2 mg of palladium acetate were added do 2.4 mL of N,N-dimethylacetamide solution containing 0.12 g of tert-butyl 2-(benzamido)-4-vinylbenzoate sequentially at room temperature and stirred under nitrogen atmosphere at 110° C. for 6 hours. After the reaction mixture was cooled to room temperature, 10% citric acid aqueous solution and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:1] to obtain 0.10 g of tert-butyl 2-(benzamido)-4-((E)-2-(4-hydroxyphenyl)vinyl)benzoate as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07999132B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-a5d03d9238174a85813931d3ff4eb88a |
|---|
| Source note | uspto-grants-2011_08 |
|---|