Tetrahydrofuran → 5-[(4-Ethenylphenyl)oxy]-2-(trifluoromethyl)pyridine

HRID 474651Notes

Reaction equation

HRID 474651 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[N:8]=[CH:7][C:6]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:22]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:14]([C:13]1[CH:16]=[CH:17][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:18])[F:1])=[N:8][CH:7]=2)=[CH:11][CH:12]=1)=[CH2:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 866662084-{[6-(Trifluoromethyl)-3-pyridinyl]oxy}benzaldehyde

Product 1

HCID 677742445-[(4-Ethenylphenyl)oxy]-2-(trifluoromethyl)pyridineYield 56.2%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 4-{[6-(trifluoromethyl)-3-pyridinyl]oxy}benzaldehyde (3.28 g, 12.28 mmol) and methyl(triphenyl)phosphonium bromide (4.39 g, 12.28 mmol) in dry THF (60 mL) was added NaH (1.718 g, 43.0 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 (1.83 g, 6.90 mmol, 56.2% yield) as light green oil. LCMS: rt=3.77 min, [M+H+]=266

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-67f671b1ee86405897a86038566d9b81
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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