Nitrogen → [5-(4-Nitro-pyrazol-1-ylmethyl)-isoxazol-3-yl]-methanol

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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 solution of 5-(4-nitro-pyrazol-1-ylmethyl)-isoxazole-3-carboxylic acid ethyl ester (3.477 g, 13.061 mmol) in THF (130.0 mL) was treated dropwise, at −78° C. with DiBAL (44.4 mL of a 1M solution in toluene, 44.41 mmol). The reaction mixture was stirred at −78° C. for 1 h followed by 1 h at rt. Sat. aq. Rochelle's salt (300 mL) was added and the reaction mixture was stirred for 2 h at rt. The aq. layer was extracted with EA (2×300 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (20:80 hept-EA) gave the title compound as a yellow oil. TLC: rf (20:80 hept-EA)=0.33. LC-MS-conditions 02: tR=0.68 min.

Provenance & Evidence