Hydrochloric Acid → 1-(2-Thienyl)-3-(4-trifluoromethoxyphenyl)-1,3-propanedione

HRID 395925

Reaction equation

HRID 395925 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1)=[O:3].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](OCC)=[O:21].[H-].[Na+].Cl>O.O1CCCC1>[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](=[O:21])[CH2:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:8][CH:9]=1)=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 76052Ethyl 2-thenoateHCID 5228211-(4-(Trifluoromethoxy)phenyl)ethan-1-one

Product 1

HCID 181756131-(2-Thienyl)-3-(4-trifluoromethoxyphenyl)-1,3-propanedioneYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Trifluoromethoxyacetophenone (4.1 g, 20 mM) and ethyl 2-thiophenecarboxylate (3.1 g, 20 mM) were placed in a 300 ml eggplant type flask, and 100 ml of dehydrated tetrahydrofuran was added thereto. After this mixture was stirred at room temperature, a 60% oil suspension of sodium hydride (1.1 g, 26 mM) was slowly added thereto. Thereafter, the resulting mixture was heated under reflux for 6 hours and allowed to cool to room temperature. After 100 ml of water was added to the reaction mixture under cooling with ice, the reaction mixture was adjusted to pH 1.0 with a concentrated aqueous solution of hydrochloric acid and then extracted with 100 ml of ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain 6.2 g of 1-(2-thienyl)-3-(4-trifluoromethoxyphenyl)-1,3-propanedione in an almost quantitative yield.

Workup

  1. additionwas slowly added
  2. temperatureThereafter, the resulting mixture was heated
  3. temperatureunder reflux for 6 hours
  4. temperatureto cool to room temperature
  5. temperatureunder cooling with ice
  6. extractionextracted with 100 ml of ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThereafter, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-84aaee33eb444d69b76e6f4e59f912b5
Source dataset
uspto-grants-2003_08
Patent number
US06605730B2

Linked notes

Loading…