N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][N:15]=[C:14]([CH:17]=[O:18])[CH:13]=2)[CH:10]=1)([O-:5])=[O:4].[CH3:19][Al](C)C.[NH4+].[Cl-].Cl>C(Cl)Cl.CCCCCCC>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][N:15]=[C:14]([CH:17]([OH:18])[CH3:19])[CH:13]=2)[CH:10]=1)([O-:5])=[O:4]
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-pyrazol-1-ylmethyl)-isoxazole-3-carbaldehyde (666 mg, 3.00 mmol) in CH2Cl2 (22.0 mL) was treated at 0° C. with trimethylaluminum (15 mL of a 1M solution in heptane, 15.00 mmol). The reaction mixture was then stirred at 0° C. for 2 h. CH2Cl2 (100.0 mL) followed by sat. aq. NH4Cl (50 mL) was then added. The mixture was then treated with 1N HCl and the aq. layer was extracted with CH2Cl2 (20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a green oil. LC-MS-conditions 02: tR=0.72 min.
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