Reacción #2164

Ecuación de reacción

2-butyne-l,4-diol

3,4-dihydro-2H-pyran

→

4-tetrahydropyranoxy-2-butyn-1-ol

Rendimiento 68.8%

Disolventes

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Otrowas evaporated
3. 3
   workup.ADDITIONthe residue was poured into 200 ml of water
4. 4
   ExtracciónThe aqueous solution was extracted with hexane (2×100 ml)
5. 5
   Extracciónre-extracted with ether (3×100 ml)
6. 6
   LavadoThe combined ether extracts were washed with 100 ml of brine
7. 7
   Secadodried over magnesium sulfate
8. 8
   Otroevaporated

Procedimiento

To a mixture of 5.0 g of 2-butyne-l,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol.

Fuente