Water → HCID 11658740, compound

HRID 356228Notes

Reaction equation

HRID 356228 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][O:13][CH2:14][O:15][CH3:16])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH3:2].CN([CH:20]=[O:21])C.O>C1COCC1.C([Li])CCC>[CH2:1]([N:3]([CH2:11][CH2:12][O:13][CH2:14][O:15][CH3:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:20]=[O:21])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 18941490HCID 18941490, compound

Product 1

HCID 11658740HCID 11658740, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 178418339ButyllithiumSolvent

Procedure

68.0 g (0.23 mol) of N-ethyl-N-[2-(methoxymethyl)oxyethyl]-4-bromoaniline was dissolved in 500 ml of anhydrous THF in an atmosphere of nitrogen, and 280 ml (2.2-fold equivalent weight) of a 1.7M n-butyllithium solution (solvent: n-pentane) was dropwise added thereto at -78° C., followed by stirring for 45 minutes. To the reaction solution obtained, 25 ml of anhydrous DMF was added, and the solution was stirred for 8 hours while allowing the temperature to naturally rise to room temperature. Thereafter, 100 ml of water was added to the resulting reaction solution, which was then extracted with dichloromethane (100 ml×2). The organic layer was dried with anhydrous sodium sulfate, and thereafter concentrated under reduced pressure. The residue thus obtained was distilled under reduced pressure to obtain 51.0 g of N-ethyl-N-[2-(methoxymethyl)oxyethyl]-4-formylaniline (yield: 91%).

Workup

  1. additionwas dropwise added
  2. customat -78° C.
  3. customTo the reaction solution obtained
  4. stirringthe solution was stirred for 8 hours
  5. customto naturally rise to room temperature
  6. extractionwas then extracted with dichloromethane (100 ml×2)
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained
  10. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-25378467ccb84ac3989399abab58aaa0
Source dataset
uspto-grants-1998_11
Patent number
US05834575

Reaction notes

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