Ethyl propiolate → Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate
Reaction equation
[N:1]1O[C:3]([O-])=[C:4]2[CH2:9][CH2:8][CH2:7][CH2:6][N+:5]=12.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[C:12]#C>C1(C)C(C)=CC=CC=1>[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]2=[CH:3][C:12]=1[C:11]([O:15][CH2:16][CH3:17])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4,5,6,7-tetrahydro[1,2,3]oxadiazolo[3,4-a]pyridin-8-ium-3-olate (Heterocycles; 1990; 31; 481), (13.0 g, 93 mmol), and ethyl propiolate (28.5 ml, 278 mmol), in xylene (250 ml) was heated under reflux for 2 hours. The cooled mixture was evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using ether as the eluant, to afford the title compound as an oil, 5.82 g.