2-(4-FLUORO-PHENYL)-OXAZOLE-4-CARBALDEHYDE synthesis

4synthesis methods

Product Name:2-(4-FLUORO-PHENYL)-OXAZOLE-4-CARBALDEHYDE
CAS Number:152940-51-7
Molecular formula:C10H6FNO2
Molecular Weight:191.16

885273-80-3 Synthesis

[2-(4-FLUORO-PHENYL)-OXAZOL-4-YL]-METHANOL

885273-80-3
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2-(4-FLUORO-PHENYL)-OXAZOLE-4-CARBALDEHYDE

152940-51-7
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Yield:152940-51-7 63%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 0 - 20; for 3 h;

Steps:

9

2-(4-Fluorophenyl)oxazole-4-carbaldehydeDess-Martin periodinane (12.8 g, 30.2 mmol) was added to a solution of (2-(4- fluorophenyl)oxazol-4-yl)methanol (4.5 g, 23.29 mmol) in dry CH₂CI₂ (90 mL) at 0 °C. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then quenched with saturated NaHC0₃ solution at 0 °C. The organic product was extracted with EtOAc. The combined extracts were washed with saturated sodium thiosulfate solution and brine. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether) to afford 2-(4-fluorophenyl)oxazole-4-carbaldehyde (2.8g, yield 63%) as a white solid. ¹ H NMR (300 MHz, CDCI₃) δ 10.01 (s, 1 H), 8.32 (s, 1 H), 8.14 - 8.10 (m, 2H), 7.23 - 7.17 (t, J = 8.8 Hz, 2H). MS (ESI) m/z: Calculated for Ci₀H₆FNO₂: 191 .04; found: 191.8 (M+H)⁺

References:

WO2011/88187,2011,A1 Location in patent:Page/Page column 52

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References

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