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

HRID 382259

反応式

HRID 382259 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-22d650afa41b488aaf13cbe9c7067d6a
出典データセット
uspto-grants-2001_10
特許番号
US06310049B1

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