Reacción #171141

Ecuación de reacción

carbon dioxide

compound 55

3,6-Dihexylthieno[3,2-b]thiophene-2-carboxylic acid

quinoline

→

compound 57

Rendimiento 68.6%

3,6-Dihexylthieno[3,2-b]thiophene

Rendimiento 68.6%

Disolventes

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro(about 2 hours)
2. 2
   Temperaturato cool to room temperature
3. 3
   LavadoThis mixture is washed repeatedly with HCl (1-2 M in water)
4. 4
   Otroto remove the quinoline
5. 5
   SecadoThe remaining organic layer is dried over MgSO4
6. 6
   Concentraciónconcentrated by evaporation
7. 7
   Otroleaving a residue, which
8. 8
   Otrois purified by column chromatography (SiO2/hexanes)

Procedimiento

A mixture of compound 55 (30 g, 0.085 mol), copper powder (3.76 g) and quinoline (80 mL) is heated at 264-260° C. in a Woods metal bath. When no further bubbles of carbon dioxide gas are detected (about 2 hours), the mixture is allowed to cool to room temperature and hexane (200 mL) is added. This mixture is washed repeatedly with HCl (1-2 M in water) to remove the quinoline. The remaining organic layer is dried over MgSO4 and concentrated by evaporation, leaving a residue, which is purified by column chromatography (SiO2/hexanes) to yield compound 57 (18 g, 68.4%). m.p. 57.5-59.1° C., 1H NMR (CD2Cl2): δ6.97 (s, 2H), 2.70 (t, 4H), 1.73 (m, 4H), 1.37 (m, 12H), 0.88 (t, 6H). 13C NMR: 136.56, 134.96, 109.80, 31.94, 29.31, 29.28, 28.47, 22.96, 14.22.

Fuente