Reaktion #457499

Reaktionsgleichung

3,4-epoxytetrahydrofuran

benzyl alcohol

magnesium perchlorate

→

trans-3-benzyloxy-4-hydroxytetrahydrofuran

Lösungsmittel

isobutyronitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a flask fitted with a condenser and nitrogen inlet
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   Sonstigethe reaction was quenched with water (1000 mL)
4. 4
   SonstigeThe phases were separated
5. 5
   Extraktionthe aqueous phase was extracted with ethyl acetate (3×400 mL)
6. 6
   TrocknenAfter drying the organic phases over MgSO4
7. 7
   Filtrationfiltering
8. 8
   Einengenconcentrating in vacuo

Vorschrift

To a flask fitted with a condenser and nitrogen inlet was added 3,4-epoxytetrahydrofuran (20 g, 0.23 mol), isobutyronitrile (100 ml, 5 vol), benzyl alcohol (124 g, 1.15 mol, 5 eq.) and finally magnesium perchlorate (10.3 g, 0.046 mol, 0.2 eq). The solution was heated at 100° C. for 24 hours. After cooling to room temperature, the reaction was quenched with water (1000 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (3×400 mL). After drying the organic phases over MgSO4, filtering and concentrating in vacuo, the trans-3-benzyloxy-4-hydroxytetrahydrofuran was isolated by column chromatography to give 29 g (66% yield) of a clear colorless liquid.

Quelle