Reacción #4551

Ecuación de reacción

2-methylbutanoic acid

4-(5-n-undecyloxy-2-pyrimidinyl)phenol

→

(s)-5-n-undecyloxy-2-[4-(2-methylbutanoyloxy)phenyl]pyrimidine

Rendimiento 70.0%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto react for one whole day at room temperature
2. 2
   OtroAfter the reaction
3. 3
   Filtraciónfilter
4. 4
   Otroseparate the insoluble matters
5. 5
   Extracciónextract the reaction product with chloroform
6. 6
   LavadoThe organic layer is washed with water, 2N hydrochloric acid and water
7. 7
   Otrodried
8. 8
   Otroevaporated
9. 9
   Otroto remove the organic solvent
10. 10
    OtroThe reaction product is purified with silica gel chromatography
11. 11
    Otrore-crystallized crystal

Procedimiento

Pour 0.328 g of 2-methylbutanoic acid synthesized from (s)-amylalcohol ([α]D23 -5.8° (neat)), 1.1 g of 4-(5-n-undecyloxy-2-pyrimidinyl)phenol, 8 ml of anhydrous chloroform and 0.662 g of 4-dimethylaminopyridine, S,S'-dicyclohexylcarbodimide into a 25 ml flask and allow to react for one whole day at room temperature. After the reaction, filter and separate the insoluble matters, and extract the reaction product with chloroform. The organic layer is washed with water, 2N hydrochloric acid and water, dried and evaporated to remove the organic solvent. The reaction product is purified with silica gel chromatography and re-crystallized crystal, and then optically active (s)-5-n-undecyloxy-2-[4-(2-methylbutanoyloxy)phenyl]pyrimidine is obtained at a yield of 70%.

Fuente