Ethanol → 5-(1-Oxo-3-thienyl-2-propenyl)-2,2'-bithiophene

HRID 1450618Notes

Reaction equation

HRID 1450618 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].[CH:14]([C:16]1[S:17][CH:18]=CC=1)=O.[OH-:21].[K+].[CH2:23](O)[CH3:24]>>[O:21]=[S:17]1[CH:16]=[CH:14][C:23]([CH:24]=[CH:2][CH2:1][C:4]2[S:8][C:7]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)=[CH:6][CH:5]=2)=[CH:18]1

Participants

5

Reactant 4

HCID 702EthanolHCID 73642-Thiophenecarboxaldehyde2×HCID 14797Potassium HydroxideHCID 6064225-Acetyl-2,2'-bithienyl

Product 1

HCID 676290955-(1-Oxo-3-thienyl-2-propenyl)-2,2'-bithiopheneYield 84.1%

Procedure

1.1 g of 5-acetyl-2,2'-bithiophene was dissolved in 35 ml of ethanol, followed by adding 0.6 ml of 2-formyl-thiophene and KOH solution (KOH: H2O : ethanol=0.5 g: 1 ml: 5 ml). The color of the solution was turned into dark brown. Additional 0.1 ml of 2-formyl-thiophene was added to complete the reaction. The reaction solution was monitored by thin layer chromatography to determine whether the reaction was completed. The reaction mixture was kept in a refrigerator overnight. Decomposed with water and the crude product was collected. After the product was recrystallized from ethanol, 1.27 g of product was thus obtained and the melting point thereof was 135°-136° C. (yield: 84.1%).

Workup

  1. customthe reaction
  2. customwas kept in a refrigerator overnight
  3. customDecomposed with water and the crude product was collected
  4. customAfter the product was recrystallized from ethanol, 1.27 g of product
  5. customwas thus obtained
  6. customthereof was 135°-136° C.

Sources & evidence

ORD record
ord-78d2c544b7ae42ed8f0176b405bfd16d
Source dataset
uspto-grants-1997_02
Patent number
US05602170

Reaction notes

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