Hydrochloric Acid → 1-[5-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-yl]-ethanol

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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-[1,2,3]triazol-2-ylmethyl)-furan-2-carbaldehyde (180 mg, 0.81 mmol) in CH2Cl2 (8.0 mL) was treated at −10° C. with trimethylaluminum (0.32 mL of a 2M solution in heptane, 0.64 mmol). The reaction mixture was stirred at 0° C. for 2 h then poured on sat. aq. NH4Cl (5 mL), diluted with CH2Cl2 (10.0 mL) followed by 1N HCl (10 mL). The mixture was extracted with CH2Cl2 (2×20 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 as a yellow oil: TLC:rf (50:50 hept-EA)=0.31. LC-MS-conditions 02: tR=0.82 min.

Provenance & Evidence