Nitrogen → 6-(4-Nitro-pyrazol-1-yl)-hexan-2-ol

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Reaction Conditions

Reaction Steps

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.

Provenance & Evidence