Réaction #72993

Équation de réaction

water

tetrahydro-4H-pyran-4-one

nitromethane

sodium ethoxide

→

4-(nitromethyl)tetrahydro-2H-pyran-4-ol

Rendement 34.0%

Solvants

ethanol

ethanol

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was transferred to a reparatory funnel
2. 2
   ExtractionThe mixture was extracted with ethyl acetate (3×900 mL)
3. 3
   Séchagedried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated to a light brown oil
6. 6
   workup.ADDITIONEthyl acetate/hexanes was added
7. 7
   Autrepale brown crystals formed
8. 8
   Autrethat were isolated by filtration
9. 9
   Autredried

Mode opératoire

A solution of tetrahydro-4H-pyran-4-one (45.0 g, 449 mmol) and nitromethane (36.5 mL, 674 mmol) in ethanol (27 mL) was treated with a solution of sodium ethoxide in ethanol (2.67 M, 8.40 mL, 22.5 mmol) using the method described in Part A of Example 9. The reaction mixture was transferred to a reparatory funnel and water (450 mL) was added. The mixture was extracted with ethyl acetate (3×900 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated to a light brown oil. Ethyl acetate/hexanes was added and pale brown crystals formed that were isolated by filtration and dried to provide 4-(nitromethyl)tetrahydro-2H-pyran-4-ol (24.4 g, 34%).

Source