Aluminum(III) Chloride → HCID 13588844, compound

HRID 1905960Notes

Reaction equation

HRID 1905960 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([CH:10]2[CH2:15][C:14](=[O:16])[O:13][C:11]2=[O:12])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[CH2:1]([C:5]1[S:9][C:8]2[CH:10]([C:11]([OH:13])=[O:12])[CH2:15][C:14](=[O:16])[C:7]=2[CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 54395479HCID 54395479, compound

Product 1

HCID 13588844HCID 13588844, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

A solution of 5.2 g (0.022 mole) of (5-isobutyl-2-thienyl)succinic anhydride in 20 cc of nitrobenzene was added drop by drop to a solution of 8 g (0.06 mole) of aluminum chloride in 40 cc of nitrobenzene. The mixture was brought to 40C for 1 hour. After cooling to ambient temperature, the reaction mixture was poured into an ice-hydrochloric acid mixture, then extracted with methylene chloride. The organic solution was extracted with an aqueous sodium carbonate solution. The aqueous phase was acidified by dilute hydrochloric acid. The oil that separated was extracted with ethyl acetate. After elimination of the solvent under reduced pressure, the residue was purified by chromatography on a silica column (9/1/0.05 methylene chloride-methanol-acetic acid eluant). 2.3 g (yield=44%) of 2-isobutyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid melting at 80° C. was obtained and used in the next stage without further purification. An analytical sample was obtained by recrystallization in a hexane-ethyl acetate mixture.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe organic solution was extracted with an aqueous sodium carbonate solution
  3. customThe oil that separated
  4. extractionwas extracted with ethyl acetate
  5. customAfter elimination of the solvent under reduced pressure, the residue was purified by chromatography on a silica column (9/1/0.05 methylene chloride-methanol-acetic acid eluant)

Sources & evidence

ORD record
ord-b146f626b5a4438fb5b496ad6992297b
Source dataset
uspto-grants-1987_03
Patent number
US04649153

Reaction notes

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