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

HRID 382259

반응식

HRID 382259 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22d650afa41b488aaf13cbe9c7067d6a
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310049B1

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