Nitrogen → (4-((4-Nitro-2H-1,2,3-triazol-2-yl)methyl)thiazol-2-yl)methanol

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Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of ethyl 4-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole-2-carboxylate (845 mg, 2.98 mmol) in THF (30 mL) was treated dropwise at 0° C. with DiBAL-H (11.3 mL of a 1.0 M solution in toluene, 11.3 mmol) and the resulting solution was stirred for 1 h at 0°. Rochelle's salt solution (100 mL) was added and the mixture was stirred for 1 h at rt. The aq. layer was extracted with EA (2×40 mL) and the combined org. layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (40:60 hept-EA)) gave the title compound as a yellow oil. TLC: rf (4:6 hept-EA)=0.25. LC-MS-conditions 07: tR=0.54 min, [M+H]+=241.95.

Provenance & Evidence