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

HRID 1582618노트

반응식

HRID 1582618 반응식
[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

참가 물질

4

반응물 2

HCID 129536551-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone2회HCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f39a97a76b154948a0e64101e0402d2a
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737434B2

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