Acetone → 5-(3-Oxo-1-butenyl)-2,2'-bithiophene

HRID 1291588Notes

Reaction equation

HRID 1291588 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)=O.[CH3:13][C:14]([CH3:16])=[O:15].[OH-].[K+].O>C(O)C>[O:15]=[C:14]([CH3:16])[CH:13]=[CH:1][C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14797Potassium HydroxideHCID 364428[2,2'-Bithiophene]-5-carboxaldehyde

Product 1

HCID 543882705-(3-Oxo-1-butenyl)-2,2'-bithiophene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
16 °C

Procedure

3.39 g of 5-formyl-2,2'-bithiophene and 2 ml of acetone was dissolved in 50 ml of ethanol. The temperature of the reaction solution was controlled at 12° C. and diluted KOH solution was dropped in. After the temperature of the mixture raised to 16° C. and the color thereof changed from dark yellow to orange red. After completion of the reaction in refrigerator for overnight, the reaction mixture was decomposed with water. The solid collected was recrystallized from alcohol. A yellowish crystal (2.23 g) was thus obtained. The melting point of the product was 204° C.

Workup

  1. customwas controlled at 12° C.
  2. customAfter completion of the reaction in refrigerator for overnight
  3. customThe solid collected
  4. customwas recrystallized from alcohol

Sources & evidence

ORD record
ord-43e75448486444a4846ceeb72be13a8d
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

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