Tetrahydrofuran → HCID 67775614, compound

HRID 705888Notes

Reaction equation

HRID 705888 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH:6]=[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>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[CH2:22])=[CH:12][CH:11]=2)[N:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 28875386HCID 28875386, compound

Product 1

HCID 67775614HCID 67775614, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde (4 g, 14.97 mmol) and methyl(triphenyl)phosphonium bromide (5.35 g, 14.97 mmol) in dry THF (40 mL) was added NaH (2.096 g, 52.4 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 (2.4 g, 9.05 mmol, 60.4% yield) as a light green oil. LCMS: rt=3.80 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-5459bbb105424184a240a619f3fb0472
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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