Réaction #45465

Équation de réaction

Water

but-3-yn-1-ol

dihyropyran

pyridinium p-toluene sulfonate

→

title compound

Rendement 98.0%

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

Rendement 98.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe layers were partitioned
2. 2
   LavageThe organic layer was washed with brine
3. 3
   Séchagedried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated under reduced pressure
6. 6
   AutreThe crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate

Mode opératoire

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).

Source