Tetrahydrofuran → 2-(3-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanol

HRID 705920Notes

Reaction equation

HRID 705920 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([CH:19]=[CH2:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[N:6]=1.B1C2CCCC1CCC2.C1C[O:33]CC1>>[F:1][C:2]1[CH:18]=[C:17]([CH2:19][CH2:20][OH:33])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[N:6]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677762762-(2-Fluoro-4-vinylphenoxy)-6-(trifluoromethyl)pyridine

Product 1

HCID 668254582-(3-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanolYield 39.1%

Procedure

To a solution of 2-(2-fluoro-4-vinylphenoxy)-6-(trifluoromethyl)pyridine (0.342 mL, 1.554 mmol) in THF (10 mL) was added 9-BBN (4.66 mL, 2.330 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (2 mL), followed by aq. NaOH (3 M, 4 mL), and 30% H2O2 (5 mL). The reaction mixture was stirred at 50° C. for 2 h. Then the THF and some water 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, concentrated and purified by flash chromatography to afford the title compound (183 mg, 39.1% yield) as a colorless oil. LCMS: rt=2.45 min

Workup

  1. customquenched with water (2 mL)
  2. stirringThe reaction mixture was stirred at 50° C. for 2 h
  3. customThen the THF and some water 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-7d3070a991394f66a0e86f456d7a523d
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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