1-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone → 4-chloro-2-(1-hydroxy-2-(1H-1-imidazolyl)-1-methylethyl)phenol

HRID 1582618Notes

Reaction equation

HRID 1582618 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:7]=1.[CH3:17][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([C:8]([OH:15])([CH3:17])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:7]=1

Participants

4

Reactant 2

HCID 129536551-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone2×HCID 178418573HCID 178418573, compound

Product 1

HCID 129728974-chloro-2-(1-hydroxy-2-(1H-1-imidazolyl)-1-methylethyl)phenolYield 24.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 1-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone [compound (5-1)] (2.37 g, 10 mmol) in tetrahydrofuran (200 mL) was added to a solution of methylmagnesium bromide in tetrahydrofuran (1 mol/L, 100 mL, 0.1 mol) under cooling with ice, and the mixture was stirred for 17 hours at room temperature. The solvent was removed, a solution of saturated ammonium chloride was added to the resultant mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure. Subsequently, the residue was purified through silica gel column chromatography and dried under reduced pressure, to thereby yield 4-chloro-2-(1-hydroxy-2-(1H-1-imidazolyl)-1-methylethyl)phenol as colorless crystals (620 mg, yield: 24.5%).

Workup

  1. temperatureunder cooling with ice
  2. customThe solvent was removed
  3. additiona solution of saturated ammonium chloride was added to the resultant mixture
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customSubsequently, the residue was purified through silica gel column chromatography
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-f39a97a76b154948a0e64101e0402d2a
Source dataset
uspto-grants-2004_05
Patent number
US06737434B2

Reaction notes

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