Reacción #955964

Ecuación de reacción

1,3-Dibromo-5-(heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

ethanol

acetic acid

HCl

→

1-bromo-5-(heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Disolventes

CHCl3

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaMixture was refluxed for one hour after which an aliquot
2. 2
   Otroreaction
3. 3
   TemperaturaAfter cooling
4. 4
   Filtraciónthe solution was filtered through fritted glass
5. 5
   Otrowas evaporated under vacuum
6. 6
   OtroProduct was obtained by silica chromatography

Procedimiento

1,3-Dibromo-5-(heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (9.43 g, 20.04 mmol) and zinc (1.31 g, 20.04 mmol) were placed in a 3 neck round-bottom flask equipped with a water condenser with ethanol (130 mL), acetic acid (40 mL) and 1 M HCl (2.5 mL). Mixture was refluxed for one hour after which an aliquot was taken for NMR analysis, which indicated reaction was complete. After cooling, the solution was filtered through fritted glass to eliminate remaining Zn particles and solvent was evaporated under vacuum. Product was obtained by silica chromatography, using a 100% hexane to 100% CHCl3 gradient.

Fuente