Potassium Carbonate → 2-(Diallylamino)-1-(5-fluoro-2-thienyl)ethanone

HRID 1618976ノート

反応式

HRID 1618976 の反応式
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([F:10])=[CH:8][CH:9]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([NH:20][CH2:21][CH:22]=[CH2:23])[CH:18]=[CH2:19]>C(#N)C.C(OCC)(=O)C.O>[CH2:17]([N:20]([CH2:21][CH:22]=[CH2:23])[CH2:2][C:3]([C:5]1[S:6][C:7]([F:10])=[CH:8][CH:9]=1)=[O:4])[CH:18]=[CH2:19]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 31279DiallylamineHCID 597069472-Bromo-1-(5-fluorothiophen-2-yl)ethanone

生成物 1

HCID 866978892-(Diallylamino)-1-(5-fluoro-2-thienyl)ethanone収率 87.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-bromo-1-(5-fluorothiophen-2-yl)ethanone (13.28 g, 59.53 mmol) in acetonitrile (298 mL) at 0° C. under nitrogen is added potassium carbonate (10.70 g, 77.39 mmol) and diallylamine (9.54 mL, 77.39 mmol). The mixture is allowed to slowly warm to room temperature with stiffing over 16 hours then diluted with ethyl acetate (500 mL) and water (200 mL). The phases are separated and the aqueous phase extracted twice with ethyl acetate (100 mL). The combined organic extracts are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with hexanes/ethyl acetate (9:1) to give the title compound (12.45 g, 87%) as a yellow oil. ES/MS (m/e): 240 (M+H).

後処理

  1. customThe phases are separated
  2. extractionthe aqueous phase extracted twice with ethyl acetate (100 mL)
  3. dry with materialThe combined organic extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with hexanes/ethyl acetate (9:1)

出典と根拠

ORDレコード
ord-164d894130fa459ba0056361aca63630
出典データセット
uspto-grants-2014_07
特許番号
US08772282B2

反応ノート

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