Reaktion #55318

Reaktionsgleichung

Propargyl chloride

3-pyridylcarbinol

sodium hydride

→

3-(2-propynyloxymethyl)pyridine

Ausbeute 45.3%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturWhile maintaining the reaction mixture at 5°-10° C.
2. 2
   workup.ADDITIONthe addition
3. 3
   Temperaturthe reaction mixture was warmed to 35°
4. 4
   Temperaturmaintained for 15 mins at this temperature
5. 5
   TemperaturThe reaction was then cooled to 15°-20°
6. 6
   Sonstigecarefully quenched by dropwise addition of water
7. 7
   Extraktionextracted with ether
8. 8
   TrocknenThe combined ether extracts were dried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Sonstigeto give 45 g crude product
12. 12
    workup.DISTILLATIONDistillation

Vorschrift

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).

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