Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 71544406 | HCID 71544406 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86680497 | HCID 86680497 | 67% |
Reaction Steps
To a stirred solution of (2-(4-fluorophenyl)thiazol-5-yl)(pyridin-4-yl)methanol (0.55 g, 1.92 mol) in DCM (20 mL) was added Dess-Martin periodinane (1.6 g, 3.84 mol) at room temperature. The resulting solution was stirred for 1 h. To the reaction mixture was added NaHCO3 solution (20 mL) and ethyl acetate (50 mL). The organic layer was extracted with ethyl acetate (2×20 mL), washed with brine solution (2×20 mL), dried over anhydrous sodium sulfate and the solvent removed via distillation under reduced pressure. The crude was purified through silica gel (100-200 mesh) column chromatography using 10% methanol in DCM) to obtain (2-(4-fluorophenyl)thiazol-5-yl)(pyridin-4-yl)methanone as off-white solid (0.4 g, 67% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.86 (d, 2H), 8.51 (s, 1H), 8.19 (dd, 2H), 7.82 (d, 2H), 7.45 (t, 2H); LC-MS m/z calculated for [M+H]+ 285.04 found 284.98.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809372B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-56942aef1cf44c3b9e4f4f8182e2e00e |
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| Source note | uspto-grants-2014_08 |
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