Aluminum(III) Chloride → ethyl 6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

HRID 424392Notes

Reaction equation

HRID 424392 reaction equation
[C:1]1([CH:7]=[C:8]([C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3]>[N+](CC)([O-])=O>[O:15]=[C:14]1[C:16]2[S:17][CH:18]=[CH:19][C:20]=2[CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 66702316Ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate

Product 1

HCID 58245847ethyl 6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

A solution of ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate (3.118 g, 10.9 mmol) and aluminum trichloride (1.725 g, 13 mmol) in nitroethane (50 ml) was heated at 75° C. for 3 hours. The reaction mixture was poured into 1N HCl-ice solution, and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and concentrated to give a brown oil. The crude product was purified via flash chromatography 9 (silica gel cartridge with eluent of 0-15% ethyl acetate/hexane) to give ethyl 6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate as am amble liquid, 3.12 g, quantitative yield. HPLC: Rt 2.873, 3.188 min.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a brown oil
  6. customThe crude product was purified via flash chromatography 9 (silica gel cartridge with eluent of 0-15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-53847b33c6aa46af80ea96fc4fc42bbd
Source dataset
uspto-grants-2012_01
Patent number
US08106046B2

Reaction notes

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