Reacción #4550

Ecuación de reacción

1-bromoctane

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

sodium hydride

→

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

Disolventes

N,N-dimethylformamide

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a cooling tube
2. 2
   Otrofor 30 minutes
3. 3
   Otroto react for 7 hours at 90° C
4. 4
   OtroAfter the reaction
5. 5
   Extracciónextract the product with ethyl acetate
6. 6
   LavadoThe organic layer is thoroughly washed with water
7. 7
   Otrodried
8. 8
   Otrothe organic solvent is evaporated
9. 9
   Otroremoved
10. 10
    Otrothe impure product is obtained
11. 11
    Otrorecrystallized

Procedimiento

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.

Fuente