Reaction #4551

Reaction equation

2-methylbutanoic acid

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

→

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

Yield 70.0%

Solvents

chloroform

Conditions

Workup

1. 1
   Otherto react for one whole day at room temperature
2. 2
   OtherAfter the reaction
3. 3
   Filtrationfilter
4. 4
   Otherseparate the insoluble matters
5. 5
   Extractionextract the reaction product with chloroform
6. 6
   WashThe organic layer is washed with water, 2N hydrochloric acid and water
7. 7
   Otherdried
8. 8
   Otherevaporated
9. 9
   Otherto remove the organic solvent
10. 10
    OtherThe reaction product is purified with silica gel chromatography
11. 11
    Otherre-crystallized crystal

Procedure

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%.

Source