Dimethylformamide → HCID 22930050, compound

HRID 1296018Notes

Reaction equation

HRID 1296018 reaction equation
[Li]CCCC.[C:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][O:18][CH3:19])([CH3:9])([CH3:8])[CH3:7].CN(C)CCN(C)C.CN(C)[CH:30]=[O:31]>CCOCC.C(OCC)(=O)C.CCCCCC>[C:6]([C:10]1[C:11]([O:16][CH2:17][O:18][CH3:19])=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH:30]=[O:31])([CH3:9])([CH3:7])[CH3:8]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 107742011-(1,1-Dimethylethyl)-2-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 22930050HCID 22930050, compoundYield 120.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 2.6 M hexane solution of n-BuLi was gradually added to a solution of the 1-(tert-butyl)-2-(methoxymethoxy)benzene (1013 g, 4.67 mol) and tetramethylethylenediamine (754 g, 6.5 ml) in dry ether while cooling on ice, and the mixture was stirred at room temperature for 3 hours. After recooling to 0° C., dimethylformamide (1000 ml, 14 mol) was gradually added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was gradually added to ice water, extraction was performed with ethyl acetate, and the organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to yield a crude product of the title compound (1247 g) as a red oil.

Workup

  1. temperaturewhile cooling on ice
  2. customAfter recooling to 0° C.
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-030e6dae5897486bbb31999f2fa8d9c5
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…