Tetrahydrofuran → 2-(4-((6-Methylpyridin-2-yl)oxy)phenyl)ethanol

HRID 705911Notes

Reaction equation

HRID 705911 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=2)=[CH:5][CH:4]=1)=[CH2:2].B1C2CCCC1CCC2.C1C[O:29]CC1>>[CH3:16][C:12]1[N: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]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677753972-[(4-Ethenylphenyl)oxy]-6-methylpyridine

Product 1

HCID 677756692-(4-((6-Methylpyridin-2-yl)oxy)phenyl)ethanolYield 128%

Procedure

To the solution of 2-[(4-ethenylphenyl)oxy]-6-methylpyridine (1.23 g, 5.82 mmol) in dry THF (20 mL), was added 9-BBN (17 mL, 8.50 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (2 mL), followed by aq. NaOH (3M, 7 mL), and 30% H2O2 (7.2 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 DCM. 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 (1.71 g, 7.46 mmol, 128% yield) as a colorless oil. LCMS: rt=2.07 min, [M+H+]=230

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 DCM
  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-2821d88156dc44f5b7f3f4f138d36e2d
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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