Lithium borohydride → HCID 90460321, compound

Participants

Reaction Steps

To a solution of ethyl 1-(4-cyanophenyl)-1H-1,2,3-triazole-5-carboxylate (650 mg, 2.68 mmol, 1.00 equiv) in THF (15 mL) at 0° C. was added LiBH4 (177.3 mg, 8.06 mmol, 3.00 equiv) in portions. The resulting solution was stirred at room temperature for 3 h and then quenched with 100 mL of saturated NH4Cl solution. The mixture was extracted with 3×100 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-50% of ethyl acetate in petroleum ether to give 200 mg (37%) of 4-[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]benzonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.12 (d, J=8.0 Hz, 2H), 7.96 (d, J=8.0 Hz, 2H), 7.90 (s, 1H), 5.60 (t, J=5.2 Hz, 1H), 4.65 (d, J=5.2 Hz, 2H) ppm. LCMS (method A, ESI): RT=1.07 min, m/z=201.0 [M+H]+.

Provenance & Evidence