Reacción #172455

Ecuación de reacción

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

Rendimiento 58.5%

Disolventes

ethyl acetate

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashing with a saturated saline solution
2. 2
   Secadodrying over anhydrous sodium sulfate, and concentration
3. 3
   OtroThe 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
   LavadoThe mixture was washed with a 5% sodium bisulfite solution
8. 8
   SecadoDrying over anhydrous magnesium sulfate and concentration
9. 9
   OtroThe residual liquid was purified by silica gel column chromatography
10. 10
    Otroto give 264 mg of a dark reddish brown oily matter (yield: 58.5%)

Procedimiento

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%).

Fuente