N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:17])[CH3:16])[CH:10]=1)([O-:5])=[O:4].CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([OH:17])[CH3:16])[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 0.1M solution of 6-(4-nitro-pyrazol-1-yl)-hexan-2-one (250 mg, 1.18 mmol) in THF was treated dropwise, at −78° C. with DiBAL (1.5 mL of a 1M solution in toluene, 1.5 mmol). The reaction mixture was stirred at −78° C. for 1 h. Sat. aq. Rochelle's salt (10 mL) was added and the reaction mixture was stirred for 2 h at rt. The aq. layer was extracted with EA (2×25 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound. TLC: rf (40:60 hept-EA)=0.2. LC-MS-conditions 02: tR=0.78 min; [M+H]+=214.23.
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