Reaktion #4551

Reaktionsgleichung

2-methylbutanoic acid

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

→

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

Ausbeute 70.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react for one whole day at room temperature
2. 2
   SonstigeAfter the reaction
3. 3
   Filtrationfilter
4. 4
   Sonstigeseparate the insoluble matters
5. 5
   Extraktionextract the reaction product with chloroform
6. 6
   WaschenThe organic layer is washed with water, 2N hydrochloric acid and water
7. 7
   Sonstigedried
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto remove the organic solvent
10. 10
    SonstigeThe reaction product is purified with silica gel chromatography
11. 11
    Sonstigere-crystallized crystal

Vorschrift

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%.

Quelle