Potassium Carbonate → (S)-3-(4-Nitro-pyrazol-1-yl)-propane-1,2-diol

Reaktionsgleichung

[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH2:9]1[O:11][C@H:10]1[CH2:12][OH:13].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][C@H:10]([OH:11])[CH2:12][OH:13])[CH:8]=1)([O-:3])=[O:2]

Komponenten

Versuchsvorschrift

3-Nitro-1-H-pyrazole (27) (600 mg, 5.3 mmol), (S)-glycidol (702 μL, 10.6 mmol) and K2CO3 (1.1 g, 8.0 mmol) in acetonitrile (7 mL) were heated in the microwave at 100° C. for 1 h. The solvent was evaporated in vacuo and the residue dissolved in ethyl acetate (20 mL) and water (20 mL). The organic layer was separated and the aqueous layer further extracted with ethyl acetate (10×20 mL). The organics were combined, dried over MgSO4, filtered and evaporated to give a crude oil. This was purified by flash chromatography on silica eluting with a gradient of 70% ethyl acetate/isohexane to ethyl acetate, to give the desired compound as a white solid (180 mg, 18%); LCMS, Rt=0.98 min (MeOH-FA method), m/z 188 (MH+).