Water → 5-Methyl-2,3-bis(4-methoxyphenyl)thiophene

HRID 579735Notes

Reaction equation

HRID 579735 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[CH2:22]([Li])CCC.CI.O>C1(C)C=CC=CC=1.C(OCC)C>[CH3:22][C:11]1[S:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 114037172,3-Bis(4-methoxyphenyl)thiopheneHCID 178418339Butyllithium

Product 1

HCID 201365185-Methyl-2,3-bis(4-methoxyphenyl)thiopheneYield 64%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3-bis(4-methoxyphenyl)thiophene (4.4 g, 15 mmole) in 100 ml of toluene was dried by distilling off 75 ml of toluene. The solution was diluted with 150 ml of diethyl ether, cooled to 0°, and treated dropwise with 1.6M n-butyl lithium (13.5 ml, 1.4 equiv.). The reaction mixture was heated at reflux for 1.5 hours, cooled to 5°, treated with a solution of methyl iodide (2 ml, 2.1 equiv.) in 10 ml of diethyl ether, and then heated at reflux for an additional 2.5 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The organic extracts were washed with 1N HCl and brine, dried, and concentrated in vacuo. Recrystallization from ethanol provided the title compound (3 g, 64%), m.p. 93°-97°. Proton nuclear magnetic resonance (NMR) was consistent with the assigned structure.

Workup

  1. distillationby distilling off 75 ml of toluene
  2. additionThe solution was diluted with 150 ml of diethyl ether
  3. temperaturecooled to 0°
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 1.5 hours
  6. temperaturecooled to 5°
  7. temperatureheated
  8. temperatureat reflux for an additional 2.5 hours
  9. customThe cooled reaction mixture
  10. extractionextracted with ethyl acetate
  11. washThe organic extracts were washed with 1N HCl and brine
  12. customdried
  13. concentrationconcentrated in vacuo
  14. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-707909c269874c039efbed72b1050260
Source dataset
uspto-grants-1988_06
Patent number
US04749712

Reaction notes

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