Reaktion #79537

Reaktionsgleichung

butyl lithium

4-pyridinecarboxaldehyde

veratrole

→

4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine

Ausbeute 81.8%

4-[1-Hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine

Ausbeute 81.8%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for about 4.5 hours
2. 2
   TemperaturThe mixture was then cooled to around 5° C.
3. 3
   Sonstigequenched with 133 mL of water
4. 4
   TemperaturThe mixture was then heated to around 80° C
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed with 67 mL of water
7. 7
   Sonstigeseparated
8. 8
   SonstigeThe residual water was removed by azeotropic distillation
9. 9
   TemperaturThe solution was then cooled to −15° C. to −5° C
10. 10
    FiltrationThe product was collected by filtration
11. 11
    Waschenwashed with 27 g of cold toluene

Vorschrift

In a 2 L flask, 48 g of veratrole was dissolved in 200 g of toluene and 138 g of butyl lithium solution (15% in hexane) were added at temperatures from 4° C. to 6° C. The mixture was stirred for one hour at about 5° C. and 3 hours at ambient temperature. Then 26.7 g of 4-pyridinecarboxaldehyde (9) in 120 g of toluene was added at around ambient temperature. The reaction mixture was stirred for about 4.5 hours. The mixture was then cooled to around 5° C. and quenched with 133 mL of water. The mixture was then heated to around 80° C. The organic layer was separated, washed with 67 mL of water and separated. The residual water was removed by azeotropic distillation. The solution was then cooled to −15° C. to −5° C. The product was collected by filtration and washed with 27 g of cold toluene. The yield was 50 g of 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine (10) (81% yield).

Quelle