3-Pyridinemethanol → 3-(2-Propynyloxymethyl)pyridine

While maintaining the reaction mixture at 5°-10° C., 3-pyridylcarbinol (50.0 g., 0.45 mol) was slowly added to a mixture of sodium hydride (24.0 g of a 50% suspension in mineral oil, 0.5 mol) in 250 ml dry N,N-dimethylformamide. Propargyl chloride (37.0 g, 0.5 mole) was then slowly added to this mixture at 15° C. Following the addition, the reaction mixture was warmed to 35° and maintained for 15 mins at this temperature. The reaction was then cooled to 15°-20°, carefully quenched by dropwise addition of water and extracted with ether. The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 45 g crude product. Distillation gave 30.0 g of 3-(2-propynyloxymethyl)pyridine. Yield 44% theory; b.p. 95° C. (0.9 mm).

1. temperatureWhile maintaining the reaction mixture at 5°-10° C.
2. additionthe addition
3. temperaturethe reaction mixture was warmed to 35°
4. temperaturemaintained for 15 mins at this temperature
5. temperatureThe reaction was then cooled to 15°-20°
6. customcarefully quenched by dropwise addition of water
7. extractionextracted with ether
8. dry with materialThe combined ether extracts were dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto give 45 g crude product
12. distillationDistillation

ORD record

ord-c848ad90b5f249fcaa1746e449176934

Source dataset

uspto-grants-1980_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04220577