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

HRID 705897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705897
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 677735132-(4-{[2-(Trifluoromethyl)-5-pyrimidinyl]oxy}phenyl)ethanolAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e604b96e4f3d4fefb64fa565175ba9e8
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

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