Methanol → 2-(3-Benzyl-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)-4-fluorophenol

HRID 916007ノート

反応式

HRID 916007 の反応式
[CH2:1]([C:8]([OH:26])([CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[O:24]C)([CH3:16])[CH3:15])[C:9]([F:12])([F:11])[F:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>ClCCl.O>[CH2:1]([C:8]([OH:26])([C:9]([F:10])([F:12])[F:11])[CH2:13][C:14]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[OH:24])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 102372232-Benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol

生成物 1

HCID 589599242-(3-Benzyl-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl)-4-fluorophenol収率 66.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 49 mg (0.13 mmol) of 2-benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (Example 4) in 0.5 mL of dichloromethane, 1 mL (1.0 mmol) of 1 M solution of boron tribromide in dichloromethane was added. The mixture was stirred at room temperature for 3 hours and was then cautiously added to cold MeOH and stirred for 20 minutes. The mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was chromatographed on silica gel using first hexanes then EtOAc-hexanes (0.5:99.5 to 1:99) to afford 31 mg (65%) of the title compound as a clear oil.

後処理

  1. stirringstirred for 20 minutes
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed on silica gel using first hexanes

出典と根拠

ORDレコード
ord-dda5af2e852a4b80819f0ced98d3bb46
出典データセット
uspto-grants-2007_09
特許番号
US07268152B2

反応ノート

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