Triethylamine → 5-(CHLOROMETHYL)-2-ETHOXYPYRIDINE
Reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.CS([Cl:23])(=O)=O>C(Cl)Cl>[Cl:23][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[N:9][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(6-Ethoxypyridin-3-yl)methanol (1.0 g, 6.5 mmol) was dissolved in methylene chloride (20 mL), and triethylamine (1.8 mL, 13 mmol) was added. The reaction mixture was cooled in an ice bath and methanesulfonyl chloride (0.67 mL, 8.6 mmol, Aldrich, Cat. 471259) was slowly added. The reaction mixture was stirred for 2 hours and then the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with MgSO4, and concentrated. The residue was purified by flash chromatograph on a silica gel column using 20% Ethyl acetate in hexane as eluent to afford the desired compound. LCMS (M+H)+: m/z=172.2.