Dimethylformamide → HCID 89157620, compound

HRID 590902Notes

Reaction equation

HRID 590902 reaction equation
[CH2:1]([CH:3]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:4][O:5][C:6]1[C:15]2[C:10](=[C:11]([O:17][CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])[C:12](Br)=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1Br)[CH3:2].C([Li])CCC.CN([CH:39]=[O:40])C.[O:41]1CCC[CH2:42]1>>[CH2:1]([CH:3]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:4][O:5][C:6]1[C:15]2[C:10](=[C:11]([O:17][CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])[C:12]([CH:42]=[O:41])=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH:39]=[O:40])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 70979723HCID 70979723, compoundHCID 178418339Butyllithium

Product 1

HCID 89157620HCID 89157620, compoundYield 45%

Conditions

Temperature
-78 °C

Procedure

After 1.0 g of 1,5-bis-(2-ethylhexyloxy)-2,6-dibromonaphthalene (1.8 mmol) was dissolved in 20 mL of tetrahydrofuran (THF), a temperature was raised to −78° C., and n-butyl lithium was slowly added thereto for 30 minutes. The mixture was stirred at −78° C. for 2 hours, and then 0.46 g of DMF (6.3 mmol) was slowly added thereto for 10 minutes and further stirred for 30 minutes. After a temperature was raised to room temperature and the reactant was stirred for 1 hour, the reaction was terminated by cool water, and the resultant was extracted with ethylacetate, followed by distillation under reduced pressure and column chromatography, thereby obtaining 1.1 g of the title compound (45.0%).

Workup

  1. waitfor 10 minutes
  2. stirringfurther stirred for 30 minutes
  3. temperatureAfter a temperature was raised to room temperature
  4. stirringthe reactant was stirred for 1 hour
  5. customthe reaction was terminated
  6. temperatureby cool water
  7. extractionthe resultant was extracted with ethylacetate
  8. distillationfollowed by distillation under reduced pressure and column chromatography

Sources & evidence

ORD record
ord-b3fa5b78f1d24e5a9611d5eead843c73
Source dataset
uspto-grants-2016_01
Patent number
US09236573B2

Reaction notes

Loading…