Reaktion #2378902

Reaktionsgleichung

sodium

imidazole

2-(biphenyl-4-yloxymethyl)-2-(3,3-dimethylprop-1-en-3-yl)-oxirane

→

4-(biphenyl-4-yloxymethyl)-3,3-dimethyl-4-hydroxy-5-(imidazol-1-yl)pent-1-ene

Ausbeute 62.5%

Lösungsmittel

n-propanol

n-propanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for two days
2. 2
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
3. 3
   workup.ADDITIONthe residue was taken up in a mixture of 150 ml of ethyl acetate and 100 ml of dichloromethane
4. 4
   Waschenthe solution was washed with three times 50 ml of water
5. 5
   TrocknenAfter the organic phase had been dried over anhydrous sodium sulphate
6. 6
   Einengenthe solution was concentrated to dryness under reduced pressure
7. 7
   workup.ADDITION10 ml of ethyl acetate were added to the solid residue
8. 8
   Filtrationthe product was filtered off

Vorschrift

35.3 g (0.120 mol) of 2-(biphenyl-4-yloxymethyl)-2-(3,3-dimethylprop-1-en-3-yl)-oxirane, dissolved in 80 ml of n-propanol, were added to a boiling solution of 1 g (0.012 mol) of sodium propylate and 9 g (0.132 mol) of imidazole in 50 ml of n-propanol, in the course of 5 minutes. After the solution had been boiled under reflux for two days, the solvent was distilled off under reduced pressure, the residue was taken up in a mixture of 150 ml of ethyl acetate and 100 ml of dichloromethane, and the solution was washed with three times 50 ml of water. After the organic phase had been dried over anhydrous sodium sulphate, the solution was concentrated to dryness under reduced pressure. 10 ml of ethyl acetate were added to the solid residue, and the product was filtered off. 27.2 g (62.5% of theory) of 4-(biphenyl-4-yloxymethyl)-3,3-dimethyl-4-hydroxy-5-(imidazol-1-yl)pent-1-ene were obtained in the form of colorless crystals of melting point 151° to 153° C. in this manner.

Quelle