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

5synthesis methods

Product Name:[2-(4-FLUORO-PHENYL)-OXAZOL-4-YL]-METHANOL
CAS Number:885273-80-3
Molecular formula:C10H8FNO2
Molecular Weight:193.17

4-Oxazolecarboxylic acid, 2-(4-fluorophenyl)-, methyl ester

1065102-64-8
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[2-(4-FLUORO-PHENYL)-OXAZOL-4-YL]-METHANOL

885273-80-3
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Yield:885273-80-3 86%

Reaction Conditions:

Stage #1: methyl 2-(4-fluorophenyl)-1,3-oxazole-4-carboxylatewith diisobutylaluminium hydride in tetrahydrofuran;toluene at -10 - 20; for 3 h;
Stage #2: with ammonium chloride in tetrahydrofuran;toluene;

Steps:

9

(2-(4-Fluorophenyl)oxazol-4-yl)methanolDIBAL-H (82 mL, 81.3 mmol, 1 M in toluene ) was added dropwise to a solution of methyl 2-(4-fluorophenyl)oxazole-4-carboxylate (6.0 g, 27.13 mmol) in dry THF (200 mL) at -10 °C. The reaction mixture was allowed to warm up to room temperature and stirred for 3 h. The reaction mixture was then quenched with saturated NH₄CI solution, filtered through Celite, and extracted with EtOAc. The combined extracts were washed with 10% aqueous NaHC0₃ solution, H₂0 and brine, dried over anhydrous Na₂S0₄, and concentrated under reduced pressure to get (2-(4-fluorophenyl)oxazol-4-yl)methanol (4.5 g, yield 86%) as a yellow solid. ¹H NMR (300 MHz, CDCI₃) δ 8.06 - 8.01 (m, 2H), 7.65 (s, 1 H), 7.18 - 7.12 (t, J = 8.7 Hz, 2H), 4.68 (s, 2H). MS (ESI) m/z: Calculated for C₁₀H₈FNO₂: 193.05; found: 193.8 (M+H)⁺