Reacción #9753

Ecuación de reacción

tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane

intermediate 76

tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane

hydrochloric acid

→

title compound

3-methyl-5-(tributylstannyl)thiophene-2-carbaldehyde

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 30 minutes
2. 2
   TemperaturaThe reaction mixture was cooled
3. 3
   Extracciónextracted thrice with diethylether
4. 4
   Extracciónextracted with saturated sodium bicarbonate
5. 5
   Secadodried with brine and over magnesium sulfate
6. 6
   OtroThe product isolated
7. 7
   Otroafter evaporation of the solvent
8. 8
   Otrowas further purified by flash column chromatography

Procedimiento

A mixture of tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane (intermediate 76, 2.92 g), 1M aqueous hydrochloric acid (3 ml) and tetrahydrofuran (10 ml) was stirred at reflux for 30 minutes. The reaction mixture was cooled, extracted thrice with diethylether. The organic solutions were combined, extracted with saturated sodium bicarbonate and dried with brine and over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (50:1) as eluent to give the title compound as a yellow oil.

Fuente