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

HRID 1844041ノート

反応式

HRID 1844041 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-efb267bb97ad4d568331775cd6c725be
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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