N,N,N',N'-Tetramethylethylenediamine → HCID 19757216, compound

HRID 1588160Notes

Reaction equation

HRID 1588160 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].CN(C)CCN(C)C.[CH2:27]([Li])[CH2:28][CH2:29][CH3:30].ICCCC>C1(C)C=CC=CC=1.CN(C)P(=O)(N(C)C)N(C)C>[CH2:27]([C:8]1[C:7]([O:9][CH2:10][O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=[C:4]([O:15][CH2:16][O:17][CH3:18])[C:3]=1[O:2][CH3:1])[CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10962Butyl iodideHCID 10061046HCID 10061046, compoundHCID 178418339Butyllithium

Product 1

HCID 19757216HCID 19757216, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

10 Grams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in 200 ml of anhydrous toluene under argon gas stream conditions, to this solution were added 50 ml of hexamethylphosphoric triamide and 8.75 ml of N,N,N',N'-tetramethylethylenediamine (TMEDA), and the mixture was cooled in a dry ice-acetone mixture bath. To this cooled mixture was added dropwise 39 ml of n-butyllithium (1.5 M, n-hexane solution), then stirred the mixture for 30 minutes. Next, 8.9 ml of 1-iodobutane was added to the reaction mixture, and the temperature was back to room temperature by taking for 12 hours. By procedures similar to those described in Reference Example 1, the above-mentioned reaction mixture was purified to obtain 8.5 g of 3-butyl-1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene. Colorless oily substance.

Workup

  1. temperaturethe mixture was cooled in a dry ice-acetone mixture bath
  2. customwas back to room temperature
  3. waitby taking for 12 hours
  4. customthe above-mentioned reaction mixture was purified

Sources & evidence

ORD record
ord-5b0304f00d6e410b979c27441099d89b
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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