Lithium borohydride → HCID 90460960, compound

Participants

Reaction Steps

To a solution of methyl 4-(4-cyanophenyl)-1,2,5-thiadiazole-3-carboxylate (260 mg, 1.06 mmol, 1.00 equiv) in anhydrous tetrahydrofuran (20 mL) maintained under nitrogen at −5° C. was added LiBH4 (117 mg, 5.32 mmol, 5.02 equiv) portion-wise. The reaction was stirred at room temperature for 1.5 h and then quenched with 5 mL of saturated NH4Cl solution. The mixture was extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with 3×100 mL of brine, dried over anhydrous sodium sulfate and concentrated to afford 230 mg (100%) of 4-(4-(hydroxymethyl)-1,2,5-thiadiazol-3-yl)benzonitrile as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6): δ 8.12 (d, J=8.4 Hz, 2H), 8.03 (d, J=8.4 Hz, 2H), 4.81 (s, 2H) ppm.

Provenance & Evidence