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

HRID 741794ノート

反応式

HRID 741794 の反応式
[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

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 5462224MagnesiumHCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneHCID 231799141-(Thiazol-2-yl)propanone

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7e48b88b910645ac9d51e4914b3797d4
出典データセット
uspto-grants-1996_09
特許番号
US05552437

反応ノート

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