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

HRID 1039176Notes

Reaction equation

HRID 1039176 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24436Sodium SulfateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-8e93e792e3394ababb9cecbcde968603
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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