Aluminum(III) Chloride → HCID 13588806, compound

HRID 1905955Notes

Reaction equation

HRID 1905955 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]2[CH2:12][C:11](=[O:13])[O:10][C:8]2=[O:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:8]([OH:10])=[O:9])[CH2:12][C:11](=[O:13])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 13787398HCID 13787398, compound

Product 1

HCID 13588806HCID 13588806, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 11.3 g (0.058 mole) of (5-methyl-2-thienyl) succinic anhydride in 30 cc of methylene chloride was added drop by drop to a mixture of 21.1 g (0.16 mole) of aluminum chloride and 50 cc of methylene chloride cooled to 0° C. The reaction mixture was stirred 5 hours at ambient temperature then poured into an ice-hydrochloric acid mixture and extracted with methylene chloride. The organic phase was separated then extracted with an aqueous sodium bicarbonate solution. The aqueous phase was acidified then, after filtration of an insoluble, again extracted with ethyl acetate. The organic extract was washed, dried on sodium sulfate and concentrated dry under reduced pressure. Recrystallization of the residue provided 3.2 g (yield=28%) of 2-methyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid (mp=140°-143° C.) identical in all respects to that obtained in example 2.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase was separated
  3. extractionthen extracted with an aqueous sodium bicarbonate solution
  4. filtrationafter filtration of an insoluble,
  5. extractionagain extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed
  8. customdried on sodium sulfate
  9. concentrationconcentrated
  10. customdry under reduced pressure
  11. customRecrystallization of the residue

Sources & evidence

ORD record
ord-2dc23efffd324381bb10a0a5c8185d04
Source dataset
uspto-grants-1987_03
Patent number
US04649153

Reaction notes

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