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

HRID 474658노트

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HRID 474658 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-ada48967ecc542f49f3309af05365527
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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