2-Chlorothiophene → Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate

HRID 747446

Reaction equation

HRID 747446 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Cl-].[CH2:8]([O:10][C:11](=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])[CH3:9].[Cl-].[Al+3].[Cl-].[Cl-]>>[Cl:1][C:2]1[S:3][C:4]([C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:19])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 72992-ChlorothiopheneHCID 6451240Aluminum(III) ChlorideHCID 86624202Adipic acid monoethyl ester chloride

Product 1

HCID 18174688Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate

Procedure

To a mixture of 2-chlorothiophene (36.0 g) and adipic acid monoethyl ester chloride (36.9 g) was added gradually aluminum chloride (50.8 g) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water (1 L) and extracted with diethyl ether (200 ml×2). The organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (200 ml), dried over anhydrous magnesium sulfate, and concentrated to give ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate as an oil (52.5 g, quantitative).

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 2 hours
  3. extractionextracted with diethyl ether (200 ml×2)
  4. washThe organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (200 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1eac7236187845369a7528bbfec57f64
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Linked notes

Loading…