Diethyl Ether → Butyl-(2,6-diethyl-benzylidene)-amine

HRID 920569Notes

Reaction equation

HRID 920569 reaction equation
[CH2:1]([N:5]=[CH:6][C:7]1[C:12](F)=[CH:11][CH:10]=[CH:9][C:8]=1F)[CH2:2][CH2:3][CH3:4].[CH2:15]([Mg]Br)[CH3:16].[CH3:19][CH2:20]OCC>C1COCC1>[CH2:1]([N:5]=[CH:6][C:7]1[C:12]([CH2:19][CH3:20])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:15][CH3:16])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58951816Butyl-(2,6-difluoro-benzylidene)-amineHCID 178418443HCID 178418443, compound

Product 1

HCID 66652926Butyl-(2,6-diethyl-benzylidene)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of butyl-(2,6-difluoro-benzylidene)-amine (1.10 g; 5.58 mmol) in THF (25 mL) was added dropwise a solution of ethylmagnesium bromide in Et2O (4.1 ml; 3.00 mol/l; 12.3 mmol) at −10° C. After the addition was completed the reaction mixture was stirred at RT for 4 hours. The reaction mixture was quenched by dropwise addition of a 5% aqueous NaHCO3-solution, and then extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to afford butyl-(2,6-diethyl-benzylidene)-amine (1.10 g).

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was quenched by dropwise addition of a 5% aqueous NaHCO3-solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee3a2b43588f482993d970cb71718331
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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