[OH:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[OH-].[K+].[CH2:11](Cl)[C:12]#[CH:13].O>CS(C)=O>[CH3:8][C:5]1[N:4]=[CH:3][C:2]([O:1][CH2:13][C:12]#[CH:11])=[CH:7][CH:6]=1To a solution of 25.0 g (0.229 mole) 3-hydroxy-6-methylpyridine in 200 ml DMSO there was added 12.8 g (0.22 mole) powdered potassium hydroxide and 20.0 g (0.266 mole) propargyl chloride. The mixture was stirred at room temperature for 6 hrs. and then poured into an equal volume of water. This mixture was extracted with ether. The ether extract was dried, filtered and concentrated to have 20.5 g crude product. Distillation gave 16.2 g 6-methyl-3-(2-propynyloxy)-pyridine. Yield 48% theory; b.p. 75° C. (1.0 mm); mp 32°-34° C.
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