Reaktion #957702

Reaktionsgleichung

potassium carbonate

4-Hydroxy-3-methoxybenzonitrile

potassium carbonate

potassium carbonate

4-(iodomethyl)-tetrahydropyran

→

title compound

3-Methoxy-4-(tetrahydro-pyran-4-ylmethoxy)-benzonitrile

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux overnight
3. 3
   Temperaturthe reaction was heated
4. 4
   workup.ADDITIONwas introduced
5. 5
   Temperaturreflux
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe material that remained was partitioned between diethyl ether and water
8. 8
   Sonstigethe aqueous phase was removed
9. 9
   Extraktionextracted with additional diethyl ether
10. 10
    SonstigeThe combined organic fractions were dried
11. 11
    Filtrationfiltered
12. 12
    Einengenthe filtrate was concentrated under reduced pressure
13. 13
    SonstigePurification by silica gel chromatography (SiO2: ethyl acetate/heptanes: 10% to 30%)

Vorschrift

1.0 g 4-Hydroxy-3-methoxybenzonitrile, 1.1 g potassium carbonate and 2.0 g 4-(iodomethyl)-tetrahydropyran were placed in 20 mL acetone and heated to reflux overnight. After this time, 1.1 g potassium carbonate was added and the reaction was heated at reflux for a further 2 h before more 0.93 g potassium carbonate was introduced and reflux was continued for a further 3 h. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The material that remained was partitioned between diethyl ether and water and the aqueous phase was removed and extracted with additional diethyl ether. The combined organic fractions were dried, filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (SiO2: ethyl acetate/heptanes: 10% to 30%) provided the title compound.

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