Chlorosuccinimide → 2-Butyl-4-chloro-5-methoxy-1-indanone

HRID 7854

反応式

HRID 7854 の反応式
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:22][CH3:23])[CH:19]=2)[C:14]1=[O:24])[CH2:10][CH2:11][CH3:12]>CN(C)C=O.CCOC(C)=O>[CH2:9]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:22][CH3:23])[C:19]=2[Cl:1])[C:14]1=[O:24])[CH2:10][CH2:11][CH3:12]

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 120457522-Butyl-5-methoxy-1-indanone

生成物 1

HCID 219909172-Butyl-4-chloro-5-methoxy-1-indanone収率 15.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-Chlorosuccinimide (505 mg, 3.8 mmol) was added to a solution of 2-butyl-5-methoxy-1-indanone (825 mg, 3.8 mmol) in anhydrous dimethylformamide (3.8 mL) and the resulting solution was stirred under nitrogen and at room temperature overnight. The reaction mixture was diluted with EtOAc (50 mL), washed with 5% aqueous NaHCO3 (20 ml), water (3×50 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by column chromatography on EM silica gel 60 (2320-400 mesh, 2.75×29 cm), eluting with CH2Cl2, to afford 2-butyl-4-chloro-5-methoxy-1-indanone (148 mg) as an oil.

後処理

  1. washwashed with 5% aqueous NaHCO3 (20 ml), water (3×50 mL) and brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was purified by column chromatography on EM silica gel 60 (2320-400 mesh, 2.75×29 cm)
  6. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-4ea1ea522fe849c09b6b48ecf0c1b923
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

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