Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acrylate | HCID 8821 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | (3R)-3-[4-Bromo-3-(trifluoromethyl)phenyl]cyclopentanone | HCID 49834553 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68759633 | HCID 68759633 | — |
Reaction Steps
To a mixture of (R)-3-(4-bromo-3-trifluoromethyl-phenyl)-cyclopentanone (Preparation 6, 1.96 g), tri(o-tolyl)phosphine (120 mg), Pd(OAc)2 (43 mg) and NaOAc (0.79 g) in DMF (13 mL) was added ethyl acrylate (0.79 g), and the reaction mixture was heated to 130° C. for 3 h. The mixture was diluted with EtOAc and washed with water. The organic phase was dried and concentrated in vacuo, and the residue was purified by flash chromatography using a gradient of heptane and EtOAc to obtain the title compound. 1H NMR (300 MHz, CDCl3) δ 8.09-7.97 (m, 1H), 7.70 (d, 1H), 7.58 (d, 1H), 7.53-7.38 (m, 1H), 6.40 (d, 1H), 4.28 (q, 2H), 3.58-3.40 (m, 1H), 2.72 (dd, 1H), 2.58-2.26 (m, 4H), 2.10-1.92 (m, 1H), 1.34 (t, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785494B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-c271d8cbf2494c0da258af7e751838fd |
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| Source note | uspto-grants-2014_07 |
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