Pyridine → HCID 86754050, compound

HRID 443050Notes

Reaction equation

HRID 443050 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH2:6]O)#[N:2].N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[I-:37].[Na+]>C(#N)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH2:6][I:37])#[N:2]

Participants

8

Reactant 4

HCID 1049PyridineHCID 5238Sodium IodideHCID 73974-Toluenesulfonyl chlorideHCID 12429902HCID 12429902, compound

Product 1

HCID 86754050HCID 86754050, compoundYield 41.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-cyano-4,4-diphenylbutan-1-ol (2.2 g, 8.7 mmol.) and pyridine (2.69 ml, 33 mmol.) in acetonitrile (20 ml) was added p-toluenesulfonyl chloride (1.66 g, 8.7 mmol.). To the mixture was added 4-dimethylaminopyridine (a catalytic amount), and the mixture was stirred for two hours at room temperature. To the reaction mixture was added ethyl acetate, which was washed with a 1N HCl and a saturated aqueous saline solution, and, then, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was dissolved in acetone (30 ml), to which was added sodium iodide (1.96 g, 13 mmol.). The mixture was refluxed for one hour. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution and a dilute aqueous solution of sodium thiosulfate, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with ethyl acetate, to afford the title compound (1.3 g).

Workup

  1. washwas washed with a 1N HCl
  2. dry with materiala saturated aqueous saline solution, and, then, dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in acetone (30 ml), to which
  5. temperatureThe mixture was refluxed for one hour
  6. distillationThe solvent was distilled off under reduced pressure
  7. additionTo the residue was added water, which
  8. extractionwas subjected to extraction with ethyl acetate
  9. washThe organic layer was washed with a saturated aqueous saline solution
  10. dry with materialby drying over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-493ccc8b810145b7b917305b9b00b853
Source dataset
uspto-grants-1999_04
Patent number
US05891916

Reaction notes

Loading…