Réaction #4550

Équation de réaction

1-bromoctane

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

sodium hydride

→

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

Solvants

N,N-dimethylformamide

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Autreequipped with a cooling tube
2. 2
   Autrefor 30 minutes
3. 3
   Autreto react for 7 hours at 90° C
4. 4
   AutreAfter the reaction
5. 5
   Extractionextract the product with ethyl acetate
6. 6
   LavageThe organic layer is thoroughly washed with water
7. 7
   Autredried
8. 8
   Autrethe organic solvent is evaporated
9. 9
   Autreremoved
10. 10
    Autrethe impure product is obtained
11. 11
    Autrerecrystallized

Mode opératoire

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.

Source