反应详情

温度

-60 °C

To a stirred mixture of LiAlH4 (259 mg, 6.82 mmol, 2.01 equiv) in anhydrous tetrahydrofuran (10 mL) maintained under nitrogen at −60° C. was added dropwise a solution of ethyl 4-(4-fluorophenyl)-1,2-oxazole-5-carboxylate (800 mg, 3.40 mmol, 1.00 equiv) in tetrahydrofuran (10 mL). The reaction mixture was stirred at −35° C. for 1 h and then quenched by 2.5 mL of saturated NH4Cl solution. The solid material was removed by filtration. The filtrate was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 10-15% of ethyl acetate in petroleum ether to give 300 mg (46%) of (4-(4-fluorophenyl)isoxazol-5-yl)methanol as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ 8.53 (s, 1H), 7.55-7.50 (m, 2H), 7.20-7.07 (m, 2H), 4.87 (s, 2H) ppm. LCMS (method C, ESI): RT=0.79 min, m/z=194.0 [M+H]+.

1. customquenched by 2.5 mL of saturated NH4Cl solution
2. customThe solid material was removed by filtration
3. dry with materialThe filtrate was dried over anhydrous sodium sulfate
4. concentrationconcentrated under vacuum
5. customThe residue was purified on a silica gel column
6. washeluted with 10-15% of ethyl acetate in petroleum ether