Methyl iodide → HCID 58056237, compound

HRID 1773551Notes

Reaction equation

HRID 1773551 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:17]I>O1CCCC1>[CH3:17][O:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5908694-Nitrobenzenebutanol

Product 1

HCID 58056237HCID 58056237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Nitrophenyl)-1-butanol (2 g, 10.26 mmol) was added, dropwise, to a suspension of sodium hydride (60% dispersion in mineral oil, 0.49 g, 12.30 mmol) in anhydrous tetrahydrofuran and the resulting mixture was stirred at room temperature for 10 minutes. Methyl iodide (2 mL) was added and the resulting mixture was stirred for 62 hours. The reaction mixture was evaporated under reduced pressure; the residue was partitioned between dichloromethane and water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (EtOAc/hexane, 1/1) to give 1.996 g of 1-(4-methoxy-butyl)-4-nitro-benzene as an oil.

Workup

  1. stirringthe resulting mixture was stirred for 62 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography (EtOAc/hexane, 1/1)

Sources & evidence

ORD record
ord-8e9165b51c354f7d987f59839a6649df
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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