Dimethylformamide → HCID 10244239, compound

HRID 654673Notes

Reaction equation

HRID 654673 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:15][CH2:16][CH3:17])[CH:8]=[CH:7][CH:6]=1.CCCCCC.C([Li])CCC.CN(C)[CH:31]=[O:32]>CCOCC.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:15][CH2:16][CH3:17])[CH:8]=[CH:7][C:6]=1[CH:31]=[O:32]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 10376810HCID 10376810, compoundHCID 178418339Butyllithium

Product 1

HCID 10244239HCID 10244239, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-35 °C

Procedure

350 g of 1-methoxymethoxy-8-propylnaphthalene was dissolved in 3 liters of absolute ether and cooled down to -35° C. 1.43 liters of a hexane solution of 1.6M n-butyl lithium was added to the solution at a temperature not higher than -30° C., followed by gradually raising the temperature and reaction at room temperature for further 1 hour. The reaction solution was again cooled down to -40° C., to which 222 ml of N,N-dimethylformamide was added in 15 minutes. The mixture was slowly raised to 10° C., to which water was added portion by portion, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate, after which it was concentrated under reduced pressure to obtain 460 g of a black reside. This residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to obtain 326 g of the captioned compound as a brown oily substance.

Workup

  1. temperatureby gradually raising
  2. customthe temperature and reaction at room temperature for further 1 hour
  3. additionwas added in 15 minutes
  4. additionwas added portion by portion
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resultant organic phase was washed with a saturated saline solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationafter which it was concentrated under reduced pressure
  9. customto obtain 460 g of a black reside
  10. customThis residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7c42b812bcda49f3843e967c7652f214
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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