Reaction #55315

Reaction equation

potassium hydroxide

2-chloro-3-pyridinol

water

propargyl chloride

→

2-chloro-3-(2-propynyloxy)pyridine

Yield 52.2%

Solvents

DMF

ether

Conditions

Workup

1. 1
   workup.STIRRINGAfter agitating
2. 2
   Otherthe organic layer was separated
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   Otherto leave 16.0 g crude product
7. 7
   OtherRecrystallization from hexane

Procedure

To a solution of 15.6 g (0.12 mole) 2-chloro-3-pyridinol in 200 ml DMF were added 6.7 g (0.12 mole) powdered potassium hydroxide. After cooling to 15° C., 9.0 g (0.12 mole) propargyl chloride was added dropwise. This mixture was stirred at room temperature for 2 hrs., then 200 ml water and 400 ml ether were added. After agitating, the organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated to leave 16.0 g crude product. Recrystallization from hexane gave 10.5 g pure 2-chloro-3-(2-propynyloxy)pyridine, mp 78°-79°.

Source