Water → 2,5-Dimethyl-3-thienyl cyclopropyl ketone

HRID 1589731Notes

Reaction equation

HRID 1589731 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][CH:6]=1.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1.[Sn](Cl)(Cl)(Cl)Cl.O>ClCCl>[CH:8]1([C:11]([C:6]2[CH:5]=[C:4]([CH3:7])[S:3][C:2]=2[CH3:1])=[O:12])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 125142,5-DimethylthiopheneHCID 24287Tin tetrachlorideHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 431614402,5-Dimethyl-3-thienyl cyclopropyl ketone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,5 Dimethylthiophene (50 g, 0.446 mole) and cyclopropylcarbonyl chloride (54.36 g, 0.52 mole) were dissolved in dichloromethane (500 ml) and cooled in an ice bath. Tin(IV) chloride (122.44 g, 0.470 mole) in dichloromethane (150 ml) was added slowly over 1 hour with stirring to form a deep red solution. The mixture was warmed to room temperature and stirred for a further hour. The mixture was then poured into cold water (750 ml) and stirred rapidly for 30 min. The dichloromethane layer was washed with cold water and dried over magnesium sulfate. The dichloromethane solvent was removed to give the ketone, 2,5-dimethyl-3-thienyl cyclopropyl ketone, as a brown oil (73.25 g).

Workup

  1. temperaturecooled in an ice bath
  2. customto form a deep red solution
  3. stirringstirred for a further hour
  4. stirringstirred rapidly for 30 min
  5. washThe dichloromethane layer was washed with cold water
  6. dry with materialdried over magnesium sulfate
  7. customThe dichloromethane solvent was removed

Sources & evidence

ORD record
ord-bb1f784aa37c4fd08eacb4796784605e
Source dataset
uspto-grants-1993_04
Patent number
US05200116

Reaction notes

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