Aluminium lithium hydride → (1-benzyl-3-nitro-1H-pyrazol-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of C2 (1.35 g, 4.90 mmol) in tetrahydrofuran (40 mL) was cooled to −40° C. and treated with lithium aluminum hydride (99%, 1 M, 10.3 mL, 10.3 mmol). The reaction was allowed to stir for 20 minutes at −40° C., then was quenched with saturated aqueous ammonium chloride solution. After addition of EtOAc and water, the layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to provide C3 as a solid. Yield: 1.29 g, 5.53 mmol, quantitative. 1H NMR (500 MHz, CDCl3) δ 2.63 (br t, J=6 Hz, 1H), 4.79 (br d, J=5.4 Hz, 2H), 5.33 (s, 2H), 7.29-7.32 (m, 2H), 7.36-7.41 (m, 3H), 7.42 (s, 1H).

Provenance & Evidence