Hydrochloric Acid → HCID 21909267, compound

HRID 1982847Notes

Reaction equation

HRID 1982847 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=1)[CH2:12]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([N:28](CC)CC)C.CS(Cl)(=O)=O.Cl>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][C:26]#[N:28])[CH:14]=[CH:15][C:16]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68873227HCID 68873227, compound

Product 1

HCID 21909267HCID 21909267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzyloxy-4-(4-ethylbenzyl)benzyl alcohol (0.87 g) in dichloromethane (20 mL) were added triethylamine (0.44 mL) and methanesulfonyl chloride (0.22 mL) at 0° C., and the mixture was stirred for 2 hours. To the reaction mixture was added 0.5 mol/L hydrochloric acid, and the mixture was extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in dimethylsulfoxide (10 mL), and potassium cyanide (0.68 g) and a catalytic amount of sodium iodide were added to the solution. The mixture was stirred at 80° C. for 12 hours. To the reaction mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1-3/1) to give [3-benzyloxy-4-(4-ethylbenzyl)phenyl]-acetonitrile (0.41 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in dimethylsulfoxide (10 mL)
  6. additionpotassium cyanide (0.68 g) and a catalytic amount of sodium iodide were added to the solution
  7. stirringThe mixture was stirred at 80° C. for 12 hours
  8. additionTo the reaction mixture was added water
  9. extractionthe mixture was extracted with diethylether
  10. washThe organic layer was washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was removed under reduced pressure
  13. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1-3/1)

Sources & evidence

ORD record
ord-cc66590a353e411289e0262925249193
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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