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Potassium Carbonate → 1-(p-Chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene

HRID 1596830
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HRID 1596830 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([F:10])[CH:8]=O)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]S(F)(=O)=O)=[CH:19][C:18]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([F:10])[CH:8]=[CH:23][C:20]2[CH:21]=[CH:22][C:17]([F:16])=[C:18]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:19]=2)=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 12113197(4-Fluoro-3-phenoxyphenyl)methanesulfonyl fluorideHCID 540115002-Fluoro-3-cyclopropyl-3-(p-chlorophenyl)acrylaldehyde

생성물 1

HCID 540353111-(p-Chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene수율 93%

시약·촉매·용매 2

HCID 2855718-Crown-6
촉매
HCID 6342Acetonitrile용매

실험 절차

A mixture of p-chloro-β-cyclopropyl-α-fluorocinnamaldehyde (224.6 mg, 1 mmol), (4-fluoro-3-phenoxyphenyl)methanesulfonyl fluoride (312.7 mg, 1.1 mmol), potassium carbonate (552.8 mg, 4 mmol), and 18-crown-6 (13.2 mg, 0.05 mmol) in acetonitrile is stirred at room temperature overnight, quenched with water, and extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product (380 mg, 94% pure by GC analysis, 93% yield) which is identified by NMR spectral analyses.

후처리

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a4e16782842a4a11afce7326db360e6d
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06291721B1

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