Reaktion #3161

Reaktionsgleichung

sodium carbonate

2-octylcoumaran-5-boronic acid

2-chloro-5-decylpyrimidine

benzene

→

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

Ausbeute 23.9%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby refluxing for 5.5 hours
2. 2
   SonstigeAfter the reaction
3. 3
   Extraktionsubjected to extraction with ethyl acetate
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknendried with mirabilite
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigeto obtain a residue
8. 8
   SonstigeThe residue was purified by silica gel column chromatography
9. 9
   Sonstigerecrystallized from a mixture solvent of toluene and methanol

Vorschrift

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##

Quelle