Potassium Cyanide → HCID 67119226, compound

HRID 2076693Notes

Reaction equation

HRID 2076693 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18]Cl)[C:13]=2[CH2:20][CH3:21])=[CH:8][CH:7]=1>C(OCC)(=O)C>[CH2:20]([C:13]1[C:14]([CH2:18][C:1]#[N:2])=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[CH:7][CH:8]=1)[CH3:21]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 67119342HCID 67119342, compound

Product 1

HCID 67119226HCID 67119226, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An aqueous solution (7 ml) of potassium cyanide (829 mg, 12.7 mmol) was added dropwise to a solution of 3′-(chloromethyl)-2′-ethyl-1,1′-biphenyl-4-yl methyl ether (3.32 g, 12.7 mmol) obtained in Example (90-4) in N,N-dimethyl sulfoxide (7 ml) at 80° C., and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1-3/1) to give (2-ethyl-4′-methoxy-1,1′-biphenyl-3-yl)acetonitrile (2.65 g, yield: 83%).

Workup

  1. washthe organic layer was successively washed with water
  2. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  3. customThe residue obtained
  4. customby removing the solvent under reduced pressure
  5. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=9/1-3/1)

Sources & evidence

ORD record
ord-39495a47905943b0b59a3ee652e91f4a
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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