Nitrogen → 4-(Ethoxymethyl)-2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)oxazole

Participants

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 2-(chloromethyl)-4-(ethoxymethyl)oxazole (260 mg, 1.48 mmol) in DMF (4.2 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (T. E. Eagles et al. Organic preparations and procedures 2 (2), 117-119, 1970; P. N. Neuman J. Heterocycl. Chem. 8, 51-56, 1971) (1.76 g of a 9.6% solution in DMF, 1.48 mmol) in DMF (4.2 mL) pre-treated for 30 min with DIPEA (0.51 mL, 2.96 mmol) and the reaction mixture was stirred overnight at 50° C. Water (20 mL), followed by EA (20 mL) was added. The layers were separated and the org. layer was washed with water (3×10 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:1 hept-EA)=0.40. LC-MS-conditions 07: tR=0.69 min, [M+H]+=254.06.

Provenance & Evidence