Ethanol → 5-[4-(5-Decylpyrimidine-2-yl)phenyl]-2-octylcoumaran

HRID 3066Notes

Reaction equation

HRID 3066 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[O:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O)C.Br[C:25]1[CH:26]=[C:27]([C:31]2[N:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:33][N:32]=2)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:37]([C:34]1[CH:35]=[N:36][C:31]([C:27]2[CH:28]=[CH:29][C:30]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[O:10][CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:17]4)=[CH:25][CH:26]=2)=[N:32][CH:33]=1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 189343232-Octylcoumaran-5-boronic acidHCID 189343242-(3-Bromophenyl)-5-decylpyrimidine

Product 1

HCID 189343135-[4-(5-Decylpyrimidine-2-yl)phenyl]-2-octylcoumaranYield 66.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

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##

Workup

  1. temperatureby refluxing for 1 hour and 40 minutes
  2. customAfter the reaction
  3. waitthe reaction mixture was left
  4. customstanding at room temperature
  5. customto precipitate a crystal
  6. washThe crystal was washed with water
  7. dissolutiondissolved in toluene
  8. dry with materialThe solution was dried with mirabilite
  9. distillationthe solvent was distilled off under reduced pressure
  10. customto obtain a residue
  11. customThe residue was purified by silica gel column chromatography
  12. customrecrystallized from a mixture solvent of toluene and methanol
  13. customfurther recrystallized from acetone

Sources & evidence

ORD record
ord-37d8555154644a60ab7cecfd4db2ff16
Source dataset
uspto-grants-1998_03
Patent number
US05733476

Reaction notes

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