Toluene → HCID 54089845, compound

HRID 1707769Notes

Reaction equation

HRID 1707769 reaction equation
I[C:2]1[N:3](CCC)[CH:4]=[N:5][C:6]=1[CH:7]=[O:8].[C:12]1(C)[CH:17]=CC=C[CH:13]=1.[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:2]1[N:3]=[C:4]([CH2:13][CH2:12][CH3:17])[NH:5][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 54325604HCID 54325604, compound

Product 1

HCID 54089845HCID 54089845, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.64 g (0.01 mol) of 4-iodo-3-n-propylimidazole-5-carboxaldehyde, 60 mL of toluene, and 0.33 g (0.00029 mol) of tetrakistriphenylphosphine palladium (0) was stirred at room temperature under nitrogen, while a solution of 2.34 g (0.0174 mol) of furan-2-ylboronic acid in 50 mL of ethanol was slowly added. The reaction was stirred for 5 minutes, after which 12 mL of 2M sodium carbonate was slowly added. After the addition was completed, the reaction was refluxed for 8 h and cooled. The reaction was filtered, the filtrate was evaporated under reduced pressure, and the resulting residue was dissolved in 300 mL of methylene chloride, washed twice with 100 mL of saturated sodium chloride solution, washed twice with 100 mL of distilled water, and washed twice with 300 mL of 10% HCl. The HCl layer was made basic with 50% sodium hydroxide until the pH=10. At this point, the basic water layer was extracted three times with 300 mL of methylene chloride, the methylene chloride layer was dried over sodium sulfate and evaporated under reduced pressure. Yield: 0.34 g (0.00156 mol, 5-carboxaldehyde. NMR (CDCl3) δ 10.14. (s,1H); 9.54 (s,1H); 7.00 (d,1H); 6.55 (m,1H); 2.79 (t,2H); 1.80 (m,2H); 1.02 (t,3H).

Workup

  1. additionwas slowly added
  2. additionAfter the addition
  3. temperaturethe reaction was refluxed for 8 h
  4. temperaturecooled
  5. filtrationThe reaction was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. dissolutionthe resulting residue was dissolved in 300 mL of methylene chloride
  8. washwashed twice with 100 mL of saturated sodium chloride solution
  9. washwashed twice with 100 mL of distilled water
  10. washwashed twice with 300 mL of 10% HCl
  11. extractionAt this point, the basic water layer was extracted three times with 300 mL of methylene chloride
  12. dry with materialthe methylene chloride layer was dried over sodium sulfate
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-51a7b3c189f849d0b016ca1aba1aad0d
Source dataset
uspto-grants-1994_10
Patent number
US05354867

Reaction notes

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