Cesium fluoride → 1-[4-(4-Chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-one

HRID 1972235노트

반응식

HRID 1972235 반응식
[F-].[Cs+].[C:3]1([CH:9]2[NH:13][C:12](=[O:14])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[C:16]1[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:18][CH:17]=1>[Cu](I)I.CNCCNC.C(OCC)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:19]2[CH:28]=[CH:29][C:16]([N:13]3[CH:9]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:10][CH2:11][C:12]3=[O:14])=[CH:17][CH:18]=2)=[CH:22][CH:23]=1

참가 물질

7

반응물 3

HCID 25953Cesium fluoride2회HCID 956722-Pyrrolidinone, 5-phenyl-HCID 193519901-Chloro-4-(4-iodophenoxy)benzene

생성물 1

HCID 569565971-[4-(4-Chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-one수율 100%

시약·촉매·용매 3

HCID 8070N,N'-Dimethylethylenediamine촉매HCID 83717Copper iodide촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

Step A (Method 2, Using CsF as Base): To a 10 mL reaction tube fitted with a screw cap is charged with 5-phenylpyrrolidin-2-one (80.5 mg, 0.5 mmol), 1-(4-iodophenoxy)-4-chlorobenzene (248 mg, 0.75 mmol, 1.5 eq), copper iodide (5.0 mg, 0.025 mmol, 0.05 eq), CsF (189 mg, 1.25 mmol, 2.5 eq), N1,N2-dimethylethane-1,2-diamine (5.5 μL, 0.05 mmol, 0.1 eq) and ethyl acetate (1 mL). The system is degassed with argon then sealed and heated to 85° C. for 20 h. The reaction is cooled to room temperature, filtered and concentrated in vacuo. Purification on silica gel (0-33% ethyl acetate in hexane) gives 1-[4-(4-chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-one as a colorless oil (182 mg, 100%).

후처리

  1. customfitted with a screw
  2. customcap
  3. customThe system is degassed with argon
  4. customthen sealed
  5. temperatureThe reaction is cooled to room temperature
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification on silica gel (0-33% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-0d1ff09e719445b38301b59a9d0d7147
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431607B2

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