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Aluminum(III) Chloride → 8-[4-(2-Hydroxyphenyl)imidazol-1-yl]octanoic acid methyl ester

HRID 1039176
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HRID 1039176 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26]C(C)C)[N:17]=[CH:16]1>C(Cl)Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>[CH3:5][O:6][C:7](=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[N:17]=[CH:16]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 591678008-[4-(2-Isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl ester

생성물 1

HCID 684892758-[4-(2-Hydroxyphenyl)imidazol-1-yl]octanoic acid methyl ester수율 59.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24436Sodium Sulfate용매

실험 절차

Add aluminum(III) chloride (3.84 g, 29 mmol) to a suspension of 8-[4-(2-isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl ester (5.16 g, 14 mmol) in methylene chloride (150 mL) at 0° C. under nitrogen. Warm the mixture to room temperature and stir for 6 hours. Dilute the mixture with saturated aqueous sodium sulfate (50 mL) and remove the solvent under reduced pressure. Dilute the residue with ethyl acetate (300 mL), wash with brine (100 mL), dry over sodium sulfate, and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (2:8 to 3:7), to provide 8-[4-(2-hydroxyphenyl)imidazol-1-yl]octanoic acid methyl ester (2.63 g, 57%).

후처리

  1. customremove the solvent under reduced pressure
  2. additionDilute the residue with ethyl acetate (300 mL)
  3. washwash with brine (100 mL)
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customPurify the residue by flash column chromatography on silica gel
  7. washeluting with ethyl acetate/hexanes (2:8 to 3:7)

출처 및 근거

ORD 기록
ord-8e93e792e3394ababb9cecbcde968603
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552039B2

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