Reaktion #4550

Reaktionsgleichung

1-bromoctane

(s)-4-[5-(6-methyl octyl)-2-pyrimidinyl]phenol

sodium hydride

→

(s)-2-[4-n-octyloxyphenyl]-5-[6-methyloctyl]pyrimidine

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a cooling tube
2. 2
   Sonstigefor 30 minutes
3. 3
   Sonstigeto react for 7 hours at 90° C
4. 4
   SonstigeAfter the reaction
5. 5
   Extraktionextract the product with ethyl acetate
6. 6
   WaschenThe organic layer is thoroughly washed with water
7. 7
   Sonstigedried
8. 8
   Sonstigethe organic solvent is evaporated
9. 9
   Sonstigeremoved
10. 10
    Sonstigethe impure product is obtained
11. 11
    Sonstigerecrystallized

Vorschrift

Pour 0.33 g of sodium hydride (about 50% oil suspension), 3 ml of dry N,N-dimethylformamide into a 30 ml three-mouth flask equipped with a cooling tube, thermometer, dripping funnel, and calcium chloride tube. Next, slowly drip 1.71 g of optically active (s)-4-[5-(6-methyl octyl)-2-pyrimidinyl]phenol which is dissolved in 6 ml of dry N,N-dimethylformamide, into the flask at room temperature. Furthermore, after reacting it for 30 minutes, add 1.10 g of 1-bromoctane, allow to react for 7 hours at 90° C. After the reaction, pour the mixture into ice water, then extract the product with ethyl acetate. The organic layer is thoroughly washed with water, dried, the organic solvent is evaporated and removed, and then the impure product is obtained. This impure product is refined with silica gel chromatography, and recrystallized to obtain 1.3 g of optically active (s)-2-[4-n-octyloxyphenyl]-5-[6-methyloctyl]pyrimidine.

Quelle