Ethyl Acetate → 7-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one

HRID 1844041노트

반응식

HRID 1844041 반응식
ClS(O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([CH2:17][CH2:18][C:19]([OH:21])=O)[CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14].C(OCC)(=O)C>CCCCCC>[F:6][C:7]1[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:10]=[C:9]2[C:8]=1[C:19](=[O:21])[CH2:18][CH2:17]2

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24638Chlorosulfonic acidHCID 467374883-[3-Fluoro-4-(trifluoromethyl)phenyl]propionic acid

생성물 1

HCID 668036517-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one수율 59%

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

Chlorosulfonic acid (12.6 mL) was added to a stirred solution of 3-(3-fluoro-4-(trifluoromethyl)phenyl)propanoic acid (I-77b: 1.0 g, 4.2707 mmol). The resulting mixture was stirred for 5 hours at 0° C. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was quenched with ice water and extracted with chloroform (2×150 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (5% ethyl acetate in hexane), afforded 550 mg of the product (58.9% yield).

후처리

  1. customThe reaction mixture was quenched with ice water
  2. extractionextracted with chloroform (2×150 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification by column chromatography on silica gel (5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-efb267bb97ad4d568331775cd6c725be
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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