Citric Acid → 3-Methyl-4-nitro-1H-pyrazole-1-ethanol

Participants

Reaction Steps

To a stirred solution of the ethyl 2-(3-methyl-4-nitropyrazol-1-yl)acetate (0.69 g, 3.24 mmol) in THF (24 mL) at −20° C. under N2 was added diisobutylaluminum hydride (1M in toluene, 6.5 mL) over 5 min. maintaining the temperature below −20° C. The solution was allowed to warm to room temperature overnight. The reaction mixture was poured into sat. aq. citric acid (60 mL). The phases were separated and the aqueous phase extracted with EtOAc (4×30 mL). The combined organic phase was washed with sat. aq. sodium potassium L-tartrate (3×20 mL) and brine (30 mL), dried (MgSO4) and the solvent removed to give 2-(3-methyl-4-nitropyrazol-1-yl)ethanol as a pale yellow oil (0.50 g, 91%). Mass spectrum: MH+ 172

Provenance & Evidence