Ethylene Glycol → 2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

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Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark under inert atmosphere (N2), a solution of 1-[5-(4-nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-yl]-ethanone (180 mg, 0.76 mmol) in ethylene glycol (0.85 mL, 15.24 mmol) was treated with trimethylorthoformate (0.17 mL, 1.52 mmol) and lithium tetrafluoroborate (14 mg, 0.15 mmol). The resulting mixture was heated to 95° C. overnight. The reaction mixture was allowed to cool to rt. NaHCO3 (10 mL) and EA (10 mL) were added and the aq. phase was extracted with EA (2×10 mL). The combined org. extracts were washed with brine (10 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:30 hept-EA) gave the title compound as a colorless oil: TLC:rf (60:30 hept-EA)=0.31. LC-MS-conditions 02: tR=0.94 min; [M+H]+=281.01.

Provenance & Evidence