Triethylamine → Ethyl 5-methyl-1,3,4-oxadiazole-2-carboxylate
Reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH3:2].C(N(CC)CC)C>C(Cl)Cl>[CH3:2][C:1]1[O:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 2-(2-acetylhydrazinyl)-2-oxoacetate (0.50 g, 2.87 mmol) in CH2Cl2 (10 mL) was added triethylamine (0.53 mL, 3.73 mmol) and p-TsCl (0.65 g, 3.44 mmol) in three portions. The reaction mixture was stirred at rt for 8 h then was diluted with CH2Cl2 and washed with water. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude was purified by column chromatography using EtOAc/hexanes to give the title compound as an off-white solid (375 mg, 84%). 1H NMR (300 MHz, CDCl3): δ 4.51 (2H, q, J=7 Hz), 2.65 (3H, s), 1.52 (3H, t, J=5 Hz). MS (M+H): 157.1.