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

HRID 1443674Notes

Reaction equation

HRID 1443674 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-0ecdacdf5a324f889c814bf21299cf79
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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