4-Toluenesulfonyl chloride → 4-(3-Chloropropyl)pyridine

Participants

Reaction Steps

To a solution of 3-pyridin-4-yl-propan-1-ol (3.1 g) in pyridine (8 mL) was added 4-methylbenzenesulfonyl chloride (5.0 g) at 0° C. The reaction mixture was stirred at RT for 12 hr. The reaction mixture was concentrated in vacuo. Saturated aqueous NaHCO3 was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=1/2) to give the title compound (2.1 g, 61%).

Provenance & Evidence