Reacción #76332

Ecuación de reacción

dioxane

aldehyde

3-bromo-4-(4-morpholinyl)benzaldehyde

2-(tributylstannyl)furan

KF

→

3-(2-furanyl)4-(4-morpholinyl)benzaldehyde

Rendimiento 84.0%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux under argon for 18 h
3. 3
   FiltraciónThe slurry was filtered through celite
4. 4
   OtroThe organic layer was separated
5. 5
   Lavadowashed with brine
6. 6
   Secadodried (MgSO4)
7. 7
   Otroevaporated to a yellow oil
8. 8
   OtroPurification by silica gel flash chromatography
9. 9
   Lavadoeluting with 20% ethyl acetate in hexane

Procedimiento

Ex-604B) To a dioxane (8 mL) solution of the aldehyde from EX-604A (0.77 g, 2.8 mmol) was added 2-(tributylstannyl)furan (1.07 mL, 3.42 mmol) and Pd(PPh3)2Cl2 (0.12 g, 0.17 mmol). The mixture was heated to reflux under argon for 18 h. The cooled mixture was poured into a mixture of saturated aq. KF and ethyl acetate and stirred 3 h. The slurry was filtered through celite. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to a yellow oil. Purification by silica gel flash chromatography eluting with 20% ethyl acetate in hexane gave 0.61 g (84%) of the desired 3-(2-furanyl)4-(4-morpholinyl)benzaldehyde product as a yellow oil. MS: m/z=258.1 [M+H]+.

Fuente