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

HRID 1582618ノート

反応式

HRID 1582618 の反応式
[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

参加物

4

反応物 2

HCID 129536551-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone2 回HCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f39a97a76b154948a0e64101e0402d2a
出典データセット
uspto-grants-2004_05
特許番号
US06737434B2

反応ノート

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