Reacción #45465

Ecuación de reacción

Water

but-3-yn-1-ol

dihyropyran

pyridinium p-toluene sulfonate

→

title compound

Rendimiento 98.0%

2-(but-3-ynyloxy)tetrahydro-2H-pyran

Rendimiento 98.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe layers were partitioned
2. 2
   LavadoThe organic layer was washed with brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated under reduced pressure
6. 6
   OtroThe crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate

Procedimiento

A solution of but-3-yn-1-ol (10.00 g, 143 mmol) in dichloromethane (310 mL) was treated with dihyropyran (18.10 g, 215 mmol) and pyridinium p-toluene sulfonate (3.60 g, 14.30 mmol). The reaction mixture was stirred at room temperature for 4 days. Water was added and the layers were partitioned. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate: heptane to give 21.57 g (98%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 4.65 (m, 1H), 3.90-3.80 (m, 2H), 3.60-3.50 (m, 2H), 2.50-2.45 (m, 2H), 1.95 (m, 1H), 1.90-1.80 (m, 1H), 1.79-1.10 (m, 1H), 1.65-1.50 (m, 4H).

Fuente