반응 #3161

반응 방정식

sodium carbonate

2-octylcoumaran-5-boronic acid

2-chloro-5-decylpyrimidine

benzene

→

5-(5-decylpyrimidine-2-yl)-2-octylcoumaran

수율 23.9%

용매

water

반응 조건

후처리

1. 1
   온도by refluxing for 5.5 hours
2. 2
   기타After the reaction
3. 3
   추출subjected to extraction with ethyl acetate
4. 4
   세척The organic layer was washed with water
5. 5
   건조dried with mirabilite
6. 6
   농축concentrated under reduced pressure
7. 7
   기타to obtain a residue
8. 8
   기타The residue was purified by silica gel column chromatography
9. 9
   기타recrystallized from a mixture solvent of toluene and methanol

실험 절차

Under nitrogen atmosphere, 0.30 g (1.09 mM) of 2-octylcoumaran-5-boronic acid, 0.26 g (1.02 mM) of 2-chloro-5-decylpyrimidine and 1.5 ml of benzene were placed in a 20 ml-round-bottomed flask. Under stirring, 0.06 g of tetrakis(triphenylphosphine) palladium (0) and 1.5 ml of a 2M-sodium carbonate aqueous solution were added to the mixture, followed by refluxing for 5.5 hours. After the reaction, the reaction mixture was poured into water and subjected to extraction with ethyl acetate. The organic layer was washed with water, dried with mirabilite and concentrated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography and recrystallized from a mixture solvent of toluene and methanol to obtain 0.11 g of 5-(5-decylpyrimidine-2-yl)-2-octylcoumaran (Ex. Comp. No-I-17) (Yield: 22.5%). The product showed the following phase transition temperatures (°C.). ##STR96##

출처