Pyridine → 2'-Methoxymethoxy-3,4-dimethoxy-2-methoxymethoxybenzophenone

HRID 1460400

반응식

HRID 1460400 반응식
N1C=CC=CC=1.O=[Cr](=O)=O.C1C=CC=CN=1.C1C=CC=CN=1.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH3:44])[C:36]=1[O:45][CH2:46][O:47][CH3:48])[OH:34].[O-][Si]([O-])=O.[Mg+2]>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](=[O:34])[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH3:44])[C:36]=1[O:45][CH2:46][O:47][CH3:48]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 61680MAGNESIUM SILICATE (synthetic)HCID 88565Trioxobis(pyridine)chromiumHCID 19812677(2-Methoxymethoxyphenyl)(3,4-dimethoxy-2-methoxymethoxyphenyl)methanol

생성물 1

HCID 198126922'-Methoxymethoxy-3,4-dimethoxy-2-methoxymethoxybenzophenone

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 6344Dichloromethane용매

실험 절차

A mixture 12.3 g (126 mmol) of chromium trioxide in 153 ml of dichloromethane was cooled to 0° C. and 20.3 ml (252 mmol) of pyridine were added with stirring to obtain, after 45 min, a yellow-brown solution (Collin's reagent). (2-Methoxymethoxyphenyl)(3,4-dimethoxy-2-methoxymethoxyphenyl)methanol (7.67 g, 21 mmol) was added with stirring and the mixture allowed to warm to room temperature with stirring overnight. Twenty grams of florisil were added and the mixture was concentrated by evaporation under reduced pressure and filtered through celite and then further eluted with ether. The resulting mixture was concentrated under reduced pressure and purified by liquid chromatography using a Waters Prep 500 Chromatograph with a silica gel column and eluting with a 70:30 mixture of hexane and ethyl acetate to obtain 6.0 g (79 percent of theory) of the title compound as an oil. The proton and carbon NMR and infrared spectra were consistent with the assigned structure.

후처리

  1. customto obtain, after 45 min
  2. stirringwith stirring
  3. stirringwith stirring overnight
  4. concentrationthe mixture was concentrated by evaporation under reduced pressure
  5. filtrationfiltered through celite
  6. washfurther eluted with ether
  7. concentrationThe resulting mixture was concentrated under reduced pressure
  8. custompurified by liquid chromatography
  9. washeluting with a 70:30 mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-77218e47e6cf4d1485d34634270218f7
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05071465

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