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

HRID 7854

반응식

HRID 7854 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 219909172-Butyl-4-chloro-5-methoxy-1-indanone수율 15.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4ea1ea522fe849c09b6b48ecf0c1b923
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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