Thionyl Chloride → 2-Chloro-3-methoxy-4-vinyl-6-(1-chloroethyl)-pyridine
Reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH:10]=[CH2:11])[CH:5]=[C:4]([CH:12](O)[CH3:13])[N:3]=1.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH:10]=[CH2:11])[CH:5]=[C:4]([CH:12]([Cl:17])[CH3:13])[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-chloro-3-methoxy-4-vinyl-6-(1-hydroxyethyl)-pyridine (446 mg, 2.09 mmol) in 10 mL of methylene chloride at 0° C. is treated with thionyl chloride (0.227 mL, 3.13 mmol) and stirred at room temperature for 1 h. The reaction is quenched with 15 mL of saturated sodium bicarbonate. The aqueous layer is extracted with 3×10 mL of methylene chloride. The combined organics are dried over potassium carbonate and concentrated in vacuo to provide 447 mg (92%) of 2-chloro-3-methoxy-4-vinyl-6-(1-chloroethyl)-pyridine.