Methyl propiolate → 4-(Methoxycarbonyl)-alpha-methyl-1H-1,2,3-triazole-1-acetic acid
Reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[N:7]([CH:10]([CH3:18])[C:11]([O:13]C(C)(C)C)=[O:12])=[N+:8]=[N-:9]>C1(C)C=CC=CC=1>[CH3:6][O:5][C:1]([C:2]1[N:9]=[N:8][N:7]([CH:10]([CH3:18])[C:11]([OH:13])=[O:12])[CH:3]=1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 1.87 g (22.3 mmol) of methyl prop-2-ynoate in 40 mL of toluene was added 1.9 g (11 mmol) of tert-butyl 2-azidopropanate. The reaction mixture was heated at 100° C. for 3 h then cooled to ambient temperature. All volatiles were removed under reduced pressure and the crude residue purified by column chromatography on silica gel eluting with a 5 to 25% acetone in hexanes gradient to afford the title compounds.