Aluminium lithium hydride → HCID 90455723, compound

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence