Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | HCID 73854978 | HCID 73854978 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 73855075 | HCID 73855075 | 33% |
Reaction Steps
To the product of Example 145 (21 mg, 32 μmol) in acetone (2 mL) was added tetra-n-butylammonium iodide (24 mg, 65 μmol). The solution was stirred at 40° C. for 17 h prior to the addition of sodium acetate (50 mg, 0.64 mmol). The reaction solution was heated at 75° C. for 48 h. After cooling the solution was diluted with EtOAc (25 mL), washed with saturated NaHCO3 (20 mL) and water (2×20 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude sample was chromatographed (silica gel, DCM) to provide the title compound (7 mg, 33%). 1H-NMR (CDCl3) δ 7.87 (1H, s), 7.60 (1H, dd), 7.30–7.35 (3H, m), 7.17–7.22 (3H, m), 6.60 (1H, dd), 6.48 (1H, d), 5.27 (2H, s), 4.72 (1H, s), 4.39 (2H, t), 4.16 (2H, t), 3.69 (2H, q), 3.16 (2H, s), 3.08 (3H, s), 2.43 (6H, s), 2.06 (3H, s), 0.91 (3H, t); MS(ESI): 675 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07115640B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-13b8291bf9004e37b3ab458c02687926 |
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| Source note | uspto-grants-2006_10 |
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