Methanol → 6-(2-Oxoethyl)nicotinonitrile
Reaction equation
[CH2:1]([C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1)[CH:2]=C.C[OH:13]>C(Cl)Cl>[O:13]=[CH:2][CH2:1][C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
A mixture of 6-(Prop-2-en-1-yl)pyridine-3-carbonitrile (4.8 g, 33 mmol) in 80 mL of DCM and 20 mL of MeOH was cooled to −70° C. Ozone was bubbled through the mixture until the mixture turned blue (about 20 minutes). The excess of ozone was removed by flush with N2 flow until the mixture turned colorless. 5 mL of Me2S was added to the mixture which was then warmed slowly to room temperature and stirred for 2 hours. The solvent was removed under vacuum below 30° C. to afford the title compound which was used without further purification.