Tetrahydrofuran → 4-ethenyl-1-methoxy-2-nitrobenzene

HRID 1773521Notes

Reaction equation

HRID 1773521 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[H-].[Na+].O1CCC[CH2:17]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:17])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 7006084-Methoxy-3-nitrobenzaldehyde

Product 1

HCID 2444164-ethenyl-1-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-methoxy-3-nitrobenzaldehyde (0.6 g) in tetrahydrofuran (10 mL) was added sodium hydride (50% suspension in mineral oil, 0.5 g) followed by methyltriphenylphosphonium bromide (1.8 g) and the resulting mixture was heated at reflux for 1 hour. The reaction mixture was cooled, diluted with water, extracted with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 90/10) to give 150 mg of 1-methoxy-2-nitro-4-vinyl-benzene.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 90/10)

Sources & evidence

ORD record
ord-52aa2831f8f94eacbf60fd804f01e747
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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