Thiophene → 2-crotonylthiophene

HRID 2254330Notes

Reaction equation

HRID 2254330 reaction equation
[C:1](O)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[S:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.ClCC(OC(=O)CCl)=O>C1(C)C=CC=CC=1>[C:1]([C:8]1[S:7][CH:11]=[CH:10][CH:9]=1)(=[O:5])/[CH:2]=[CH:3]/[CH3:4]

Participants

5

Reactant 3

HCID 8030ThiopheneHCID 10946Chloroacetic anhydrideHCID 637090Crotonic Acid

Product 1

HCID 53858592-crotonylthiopheneYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 4.31 g (0.05 mole) of crotonic acid, 5.47 g (0.065 mole) of thiophene and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution was added 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was stirred at 50° C. for 6.5 hours. After completion of the reaction, the reaction solution was cooled and washed with 5% aqueous sodium carbonate solution and water in this order. The organic layer was concentrated under reduced pressure to obtain 4.26 g of 2-crotonylthiophene.

Workup

  1. additionTo the resulting solution was added 0.71 g of boron trifluoride-diethyl ether complex
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled
  4. washwashed with 5% aqueous sodium carbonate solution and water in this order
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-561c2d433dae4eeabc68cbb222493a9f
Source dataset
uspto-grants-1993_08
Patent number
US05235068

Reaction notes

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