Tetrahydrofuran → 2-(4-{[6-(Trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethanol

HRID 705891Notes

Reaction equation

HRID 705891 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][CH:15]=2)=[CH:5][CH:4]=1)=[CH2:2].B1C2CCCC1CCC2.C1C[O:32]CC1>>[F:18][C:16]([F:19])([F:17])[C:13]1[N:14]=[CH:15][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH2:2][OH:32])=[CH:8][CH:7]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677742445-[(4-Ethenylphenyl)oxy]-2-(trifluoromethyl)pyridine

Product 1

HCID 677763732-(4-{[6-(Trifluoromethyl)-3-pyridinyl]oxy}phenyl)ethanolYield 137%

Procedure

To the solution of 5-[(4-ethenylphenyl)oxy]-2-(trifluoromethyl)pyridine (1.83 g, 6.90 mmol) in dry THF (20 mL), was added 9-BBN (20.70 mL, 10.35 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (2 mL), followed by aq. NaOH (3M, 9 mL), and 30% H2O2 (8 mL). The reaction mixture was heated at 50° C. for 3 h. Then THF was removed under reduced pressure, and the residue was diluted with EA. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated and purified by flash chromatography to afford the title compound (2.67 g, 9.43 mmol, 137% yield) as a colorless oil. LCMS: rt=2.97 min, [M+H+]=284

Workup

  1. customquenched with water (2 mL)
  2. temperatureThe reaction mixture was heated at 50° C. for 3 h
  3. customThen THF was removed under reduced pressure
  4. additionthe residue was diluted with EA
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3b9c2beb54b34a08a83396dd3c02c3c2
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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