Tetrahydrofuran → 5-fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl](O-benzyl)phenol

HRID 741794노트

반응식

HRID 741794 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[S:18]1[CH:22]=[CH:21][N:20]=[C:19]1[CH2:23][C:24](=O)[CH3:25].C1C[O:30]CC1>>[F:15][C:13]1[CH:12]=[C:11]([C:23]([OH:30])([C:19]2[S:18][CH:22]=[CH:21][N:20]=2)[CH2:24][CH3:25])[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 5462224MagnesiumHCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneHCID 231799141-(Thiazol-2-yl)propanone

생성물 1

HCID 199096325-fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl](O-benzyl)phenol수율 50%

실험 절차

A solution of 3-benzyloxy-1-bromo-5-fluorobenzene (EP: 0385662, ICI, Pharma) (5.4 g, 19.4 mmol) in dry THF (30 mL) containing magnesium (941 mg, 38.7 mmol) was heated until the Grignard reagent was formed then the reaction mixture was stirred at r.t. for 30 min. and transferred to a solution of 1-(thiazol-2-yl)propanone in dry THF at 0° C. The reaction mixture was stirred for 30 min. then an aqueous solution of NH4OAc (25%) was added and the THF evaporated. The residue was diluted with EtOAc and washed successively with H2O, brine, dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane:EtOAc 9:1 to give 2.2 g, (50%) of the title product.

후처리

  1. customwas formed
  2. stirringThe reaction mixture was stirred for 30 min.
  3. customthe THF evaporated
  4. additionThe residue was diluted with EtOAc
  5. washwashed successively with H2O, brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-7e48b88b910645ac9d51e4914b3797d4
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552437

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