Tetrahydrofuran → HCID 67775480, compound

HRID 705883Notes

Reaction equation

HRID 705883 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH: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:7]=[CH:8][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=2)=[CH:11][CH:12]=1)=[CH2:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 133008444-(4-(Trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 67775480HCID 67775480, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 4-{[4-(trifluoromethyl)phenyl]oxy}benzaldehyde (4.68 g, 17.58 mmol) and methyl(triphenyl)phosphonium bromide (6.28 g, 17.58 mmol) in dry THF (50 mL) was added NaH (3 g, 75 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 3 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (890 mg, 19% yield) as a light green oil. LCMS: rt=4.19 min, [M+H+]=265

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-58ca4ac3da5647ada3aa4b20789b4222
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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