Hydrochloric Acid → HCID 21909267, compound

HRID 1826649Notes

Reaction equation

HRID 1826649 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 aqueous hydrochloric acid solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reducer pressure. The residue was dissolved in dimethyl sulfoxide (10 mL). To the solution were added potassium cyanide (0.68 g) and a catalytic amount of sodium iodide, and the resulting mixture was stirred at 80° C. for 12 hours. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. 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 solution, and dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reducer pressure
  5. dissolutionThe residue was dissolved in dimethyl sulfoxide (10 mL)
  6. additionTo the solution were added potassium cyanide (0.68 g)
  7. stirringa catalytic amount of sodium iodide, and the resulting mixture was stirred at 80° C. for 12 hours
  8. additionWater was added to the reaction mixture
  9. extractionthe mixture was extracted with diethyl ether
  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-81ddbbccfae24f2dab79f7a261c0b887
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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