Tetrahydrofuran → 2-[(4-Ethenylphenyl)oxy]-6-methylpyridine

HRID 474671Notes

Reaction equation

HRID 474671 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:13]([C:12]1[CH:15]=[CH:16][C:9]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:10][CH:11]=1)=[CH2:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 866662114-[(6-Methyl-2-pyridinyl)oxy]benzaldehyde

Product 1

HCID 677753972-[(4-Ethenylphenyl)oxy]-6-methylpyridineYield 51.1%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 4-[(6-methyl-2-pyridinyl)oxy]benzaldehyde (2.43 g, 11.40 mmol) and methyl(triphenyl)phosphonium bromide (4.07 g, 11.40 mmol) in dry THF (30 mL) was added NaH (1.595 g, 39.9 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 2 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (1.23 g, 5.82 mmol, 51.1% yield) as a light green oil. LCMS: rt=3.27 min, [M+H+]=212

Workup

  1. washThe organic layer was washed three times with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-57139d316ff641a189e2a1002e8821f3
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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