Reaktion #172455

Reaktionsgleichung

water

potassium carbonate

5-[2-(4-dibutylamino-2-hydroxyphenyl) vinyl]thiophene-2-carboaldehyde

epibromohydrin

→

5-[2-[4-dibutylamino-2-(oxiranylmethoxy)phenyl]vinyl]thiophene-2-carboaldehyde

Ausbeute 58.5%

Lösungsmittel

ethyl acetate

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashing with a saturated saline solution
2. 2
   Trocknendrying over anhydrous sodium sulfate, and concentration
3. 3
   SonstigeThe residue was purified by silica gel column chromatography
4. 4
   workup.DISSOLUTIONThe oily matter was dissolved in 50 ml of ether
5. 5
   workup.ADDITION10 mg of iodine was added
6. 6
   workup.STIRRINGThe mixture was stirred for 1 hour
7. 7
   WaschenThe mixture was washed with a 5% sodium bisulfite solution
8. 8
   TrocknenDrying over anhydrous magnesium sulfate and concentration
9. 9
   SonstigeThe residual liquid was purified by silica gel column chromatography
10. 10
    Sonstigeto give 264 mg of a dark reddish brown oily matter (yield: 58.5%)

Vorschrift

In 10 ml of acetonitrile were dissolved 390 mg (1.09 mmol) of 5-[2-(4-dibutylamino-2-hydroxyphenyl) vinyl]thiophene-2-carboaldehyde and 0.22 g (1.61 mmol) of epibromohydrin. To this mixture were added 0.3 g (2.17 mmol) of anhydrous potassium carbonate and 40 mg of tetrabutylammonium iodide, and the mixture was stirred with heating at 60° C. for 4 hours. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography. The oily matter was dissolved in 50 ml of ether and 10 mg of iodine was added thereto. The mixture was stirred for 1 hour. The mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution. Drying over anhydrous magnesium sulfate and concentration were performed. The residual liquid was purified by silica gel column chromatography to give 264 mg of a dark reddish brown oily matter (yield: 58.5%).

Quelle