Reaction #816410

Reaction equation

product

4-Bromo-3-thiophene-formamide

tributylstannyl(trimethylsilyl)acetylene

→

4-(trimethylsilyl)ethinyl-3-thiophene formamide

Yield 27.7%

Conditions

Workup

1. 1
   Otherinto degassed toluene (20 ml)
2. 2
   Temperaturethe mixture was heated
3. 3
   Temperatureunder reflux for 16 hours under an atmosphere of nitrogen
4. 4
   TemperatureAfter cooling
5. 5
   Otherthe solvent was removed
6. 6
   Otherthe residue was chromatographed on silica gel (hexane:ethylacetate 3:1)
7. 7
   OtherAfter three consecutive crystallisations from hexane

Procedure

The product from step B (1 g), tributylstannyl(trimethylsilyl)acetylene (2.16 g) and palladium(tetrakis)triphenylphoshine (0.28 g) were placed into degassed toluene (20 ml) and the mixture was heated under reflux for 16 hours under an atmosphere of nitrogen. After cooling, the solvent was removed and the residue was chromatographed on silica gel (hexane:ethylacetate 3:1). After three consecutive crystallisations from hexane, 0.3 g of 4-(trimethylsilyl)ethinyl-3-thiophene formamide was obtained (m.p. 90-94° C.).

Source