Dimethyl Sulfoxide → HCID 19759261, compound

HRID 248375Notes

Reaction equation

HRID 248375 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([CH:19]=O)[CH:16]=[C:15]2[C:21]#[N:22])=[CH:10][CH:9]=1)=[O:7])[CH3:4].[CH3:23]S(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([CH:19]=[CH2:23])[CH:16]=[C:15]2[C:21]#[N:22])=[CH:10][CH:9]=1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 19759475HCID 19759475, compound

Product 1

HCID 19759261HCID 19759261, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Conditions

Temperature
60 °C

Procedure

To a solution of dimethylsulfoxide (64 ml) was added sodium hydride (480 mg, 60% oil dispersion) at ambient temperature. The suspension was stirred at 60° C. for 50 minutes to give a clear solution. To the cooled solution was added methyltriphenylphosphonium bromide (4.29 g) at ambient temperature in one portion. The mixture was stirred at ambient temperature for half an hour and at 50° C. for half an hour. The yellow mixture was cooled to ambient temperature and therein 1-(4-ethoxycarbonylphenyl)-4-formylpyrrole-2-carbonitrile (2.68 g) was added in one portion. After stirring at ambient temperature for one and half hours, the mixture was quenched with aqueous hydrochloric acid and extracted with dichloromethane. The organic layer was washed with aqueous hydrochloric acid three times, dried, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted by 20% n-hexane in dichloromethane to yield 1-(4-ethoxycarbonylphenyl)-4-vinylpyrrole-2-carbonitrile (1.80 g) as a white solid.

Workup

  1. customto give a clear solution
  2. stirringThe mixture was stirred at ambient temperature for half an hour and at 50° C. for half an hour
  3. temperatureThe yellow mixture was cooled to ambient temperature
  4. stirringAfter stirring at ambient temperature for one and half hours
  5. customthe mixture was quenched with aqueous hydrochloric acid
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed with aqueous hydrochloric acid three times
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel
  11. washeluted by 20% n-hexane in dichloromethane

Sources & evidence

ORD record
ord-3510c7b864e242a1a5cbb1dc902d73de
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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