Potassium Permanganate → 5-Methoxy-3-propyl-1-indanone

HRID 7876

반응식

HRID 7876 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=1.[O-:15][Mn](=O)(=O)=O.[K+]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:15])[CH2:8][CH:9]2[CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 2

HCID 516875Potassium PermanganateHCID 219909336-Methoxy-1-propyl-indan

생성물 1

HCID 219908595-Methoxy-3-propyl-1-indanone수율 15.1%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 6344Dichloromethane용매

실험 절차

The mixture of indans from step 2 (1.287 g, approx. 6.1 mmol) in CH2Cl2 (50 mL) was treated with a finely ground mixture of KMnO4 (7.00 g) and CuSO4.xH2O. The resulting mixture was heated at reflux for 89 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was dried over MgSO4, filtered and evaporated under vacuum to an oil (1.155 g). The crude product was purified by chromatography on a Biotage FLASH 12M column, eluting with 10% EtOAc in hexanes, to afford 5-methoxy-3-propyl-1-indanone (0.188 g) as an oil. Other column fractions afforded 6-methoxy-3-propyl-1-indanone, the indan starting materials, and 5-methoxy-1-indanone.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 89 hours
  3. filtrationfiltered through a celite pad
  4. dry with materialThe filtrate was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to an oil (1.155 g)
  7. customThe crude product was purified by chromatography on a Biotage FLASH 12M column
  8. washeluting with 10% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-3f65a22cc30c4c71b7a3d15e3263d86d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

연결된 노트

불러오는 중…