Reaktion #3162

Reaktionsgleichung

sodium carbonate

2-octylcoumaran-5-boronic acid

ethanol

2-(3-bromophenyl)-5-decylpyrimidine

→

5-[4-(5-decylpyrimidine-2-yl)phenyl]-2-octylcoumaran

Ausbeute 66.5%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby refluxing for 1 hour and 40 minutes
2. 2
   SonstigeAfter the reaction
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   Sonstigestanding at room temperature
5. 5
   Sonstigeto precipitate a crystal
6. 6
   WaschenThe crystal was washed with water
7. 7
   workup.DISSOLUTIONdissolved in toluene
8. 8
   TrocknenThe solution was dried with mirabilite
9. 9
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
10. 10
    Sonstigeto obtain a residue
11. 11
    SonstigeThe residue was purified by silica gel column chromatography
12. 12
    Sonstigerecrystallized from a mixture solvent of toluene and methanol
13. 13
    Sonstigefurther recrystallized from acetone

Vorschrift

Under nitrogen atmosphere, 0.25 g (0.91 mM) of 2-octylcoumaran-5-boronic acid, 0.7 ml of ethanol, 0.30 g (0.80 mM) of 2-(3-bromophenyl)-5-decylpyrimidine and 1.3 ml of benzene were placed in a 20 ml-round-bottomed flask. Under stirring, 0.05 g of tetrakis(triphenylphosphine) palladium (0) and 1.3 ml of a 2M-sodium carbonate aqueous solution were added successively to the mixture, followed by refluxing for 1 hour and 40 minutes. After the reaction, the reaction mixture was left standing at room temperature to precipitate a crystal. The crystal was washed with water and dissolved in toluene. The solution was dried with mirabilite and the solvent was distilled off 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 and further recrystallized from acetone to obtain 0.28 g of 5-[4-(5-decylpyrimidine-2-yl)phenyl]-2-octylcoumaran (Ex. Comp. No. I-154) (Yield: 66.5%). The product showed the following phase transition temperatures (°C.). ##STR98##

Quelle