Reaction #3161

Reaction equation

sodium carbonate

2-octylcoumaran-5-boronic acid

2-chloro-5-decylpyrimidine

benzene

→

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

Yield 23.9%

Solvents

water

Conditions

Workup

1. 1
   Temperatureby refluxing for 5.5 hours
2. 2
   OtherAfter the reaction
3. 3
   Extractionsubjected to extraction with ethyl acetate
4. 4
   WashThe organic layer was washed with water
5. 5
   Dryingdried with mirabilite
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   Otherto obtain a residue
8. 8
   OtherThe residue was purified by silica gel column chromatography
9. 9
   Otherrecrystallized from a mixture solvent of toluene and methanol

Procedure

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##

Source