2,2'-Bithiophene → (2,2':5',2''-Terthiophene)-5-carboxaldehyde

HRID 1291589Notes

Reaction equation

HRID 1291589 reaction equation
I[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1>C(#N)C.[Hg]>[CH:7]([C:5]1[S:6][C:2]([C:13]2[S:9][C:10]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[CH:11][CH:12]=2)=[CH:3][CH:4]=1)=[O:8]

Participants

5

Reactant 2

HCID 681202,2'-BithiopheneHCID 30143612-Thiophenecarboxaldehyde, 5-iodo-

Product 1

HCID 454742(2,2':5',2''-Terthiophene)-5-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 6342AcetonitrileSolvent

Procedure

1 g of 5-iodo-2-thiophenecarboxaldehyde was dissolved in 200 ml of acetonitrile. 0.7 g of bithiophene was added into the solution under nitrogen gas atmosphere for 1 hour and irradiated under 100 W mercury-vapor lamp light for 12 hours. The solution was monitored by thin layer chromatography. At this stage, about 60% product was generated. The acetonitrile was removed from the reaction solution under reduced pressure and CH2Cl2 was added for extraction. After the extract was filtered through silica gel layer and separated by column chromatography, starting material was recovered from the eluate of ethyl acetate/n-hexane 1/9 fraction and 5-formyl-2,2':5',2"-terthiophene was obtained from the eluate of ethyl acetate/n-hexane 3/7 fraction respectively.

Workup

  1. customThe acetonitrile was removed from the reaction solution under reduced pressure and CH2Cl2
  2. additionwas added for extraction
  3. filtrationAfter the extract was filtered through silica gel layer
  4. customseparated by column chromatography
  5. customwas recovered from the eluate of ethyl acetate/n-hexane 1/9 fraction

Sources & evidence

ORD record
ord-2427d5ef74a3430d87bf5240c1113068
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

Loading…