Hydrogen Peroxide → 2-(4-{[2-(Trifluoromethyl)-5-pyrimidinyl]oxy}phenyl)ethanol

HRID 474658ノート

反応式

HRID 474658 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][CH:15]=2)=[CH:5][CH:4]=1)=[CH2:2].B1C2CCCC1CCC2.[OH-:29].[Na+].OO>C1COCC1>[F:17][C:16]([F:19])([F:18])[C:13]1[N:12]=[CH:11][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH2:2][OH:29])=[CH:8][CH:7]=2)=[CH:15][N:14]=1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677758455-[(4-Ethenylphenyl)oxy]-2-(trifluoromethyl)pyrimidine

生成物 1

HCID 677735132-(4-{[2-(Trifluoromethyl)-5-pyrimidinyl]oxy}phenyl)ethanol収率 74.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of 5-[(4-ethenylphenyl)oxy]-2-(trifluoromethyl)pyrimidine (100 mg, 0.376 mmol) and 9-BBN (1.503 mL, 0.751 mmol) in THF (5 mL) under nitrogen, which was stirred overnight was added NaOH (0.501 mL, 1.503 mmol) and H2O2 (0.460 mL, 4.51 mmol). The mixture was heated at 60° C. for 1 h, and then quenched with NH4Cl sat. solution after cooling. The organic layer was separated and washed with Na2SO3 solution and brine. The organic layer was dried by Na2SO4. Concentration then afforded the title compound (80 mg, 0.281 mmol, 74.9% yield). LCMS: rt=2.82 min, [M+H+]=285

後処理

  1. customquenched with NH4Cl sat. solution
  2. temperatureafter cooling
  3. customThe organic layer was separated
  4. washwashed with Na2SO3 solution and brine
  5. dry with materialThe organic layer was dried by Na2SO4
  6. concentrationConcentration

出典と根拠

ORDレコード
ord-ada48967ecc542f49f3309af05365527
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

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