Potassium Carbonate → HCID 67456227, compound

HRID 1713291Notes

Reaction equation

HRID 1713291 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].[CH2:22]([O:29][CH2:30][CH2:31][CH2:32][CH2:33]Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][O:1][C:2]1[CH:3]=[C:4]([CH2:5][NH2:6])[CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4422181((4-Bromobutoxy)methyl)benzeneHCID 21797966HCID 21797966, compound

Product 1

HCID 67456227HCID 67456227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-hydroxy-4-phenylbenzonitrile (0.600 g) in N,N-dimethylformamide (4.1 mL) was added potassium carbonate (0.850 g). Then 4-benzyloxy-1-bromobutane (0.703 mL) was added, and the resulting mixture was stirred at 50° C. for 26.5 hours. The reaction mixture was cooled to room temperature and then partitioned between diethyl ether (35 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue (1.25 g) was dissolved in tetrahydrofuran (13 mL) and added to an ice-cold suspension of lithium alminiumhydride (0.175 g) in tetrahydrofuran (18 mL), and the resulting mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature and then quenched by sequential addition of water (0.175 mL), 15% aqueous sodium hydroxide (0.175 mL) and water (0.175 mL). After addition of anhydrous sodium sulfate (10.4 g), the mixture was stirred at room temperature for 13 hours and the insoluble material was filtered out. The filtrate was concentrated under reduced pressure to give the title compound (1.21 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between diethyl ether (35 mL) and water (10 mL)
  3. washThe organic layer was washed successively with water (10 mL×2) and brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue (1.25 g) was dissolved in tetrahydrofuran (13 mL)
  7. additionadded to an ice-cold suspension of lithium alminiumhydride (0.175 g) in tetrahydrofuran (18 mL)
  8. stirringthe resulting mixture was stirred at 60° C. for 2 hours
  9. temperatureThe reaction mixture was cooled to room temperature
  10. customquenched by sequential addition of water (0.175 mL), 15% aqueous sodium hydroxide (0.175 mL) and water (0.175 mL)
  11. additionAfter addition of anhydrous sodium sulfate (10.4 g)
  12. stirringthe mixture was stirred at room temperature for 13 hours
  13. filtrationthe insoluble material was filtered out
  14. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4d1be1b113b049acb6f8e34d6471096f
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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