Lithium borohydride → HCID 90456052, compound

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Reaction Steps

To a stirred solution of ethyl 4-(4-cyanophenyl)-1,3-oxazole-5-carboxylate (347 mg, 1.43 mmol, 1.00 equiv) in anhydrous THF (5 mL) maintained at −5° C. was added LiBH4 (157 mg, 7.14 mmol, 4.98 equiv) in several portions. The resulting solution was stirred at room temperature for 3 h then quenched by the addition of 10 mL of saturated NH4Cl solution. The mixture was extracted with 2×10 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum to give 190 mg (66%) of 4-(5-(hydroxymethyl)oxazol-4-yl)benzonitrile as a yellow solid. LCMS (method D, ESI): RT=1.13 min, m/z=201.0 [M+H]+.

Provenance & Evidence