Dimethylformamide → 3-(1-Phenylvinyl)benzaldehyde

HRID 2422255

Reaction equation

HRID 2422255 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:9])[CH:3]=1.C([Li])CCC.CCCCCC.CN(C)[CH:29]=[O:30].[Cl-].[NH4+]>O1CCCC1>[C:10]1([C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH:29]=[O:30])=[CH2:9])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 230831781-Bromo-3-(1-phenylethenyl)benzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 131027463-(1-Phenylvinyl)benzaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromo-3-(1-phenylvinyl)benzene (1.00 g, 3.86 mmol) in tetrahydrofuran (5 mL) was stirred under a nitrogen atmosphere at −78° C., and 1.6 M n-butyllithium/hexane solution (3 mL, 4.8 mmol) was added dropwise. After 1 hr, N,N-dimethylformamide (0.372 mL, 4.80 mmol) was added, and the mixture was further stirred at the same temperature for 2 hrs. Aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane) to give the title compound (0.626 g, yield 78%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-941befe5b50a4bd3a22e0dda6c60842f
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Linked notes

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