Reaktion #83536

Reaktionsgleichung

potassium carbonate

3-benzyloxy-2-iodopyridine

acrylic acid methyl ester

→

3-(3-benzyloxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture is concentrated by evaporation in a vacuum
2. 2
   workup.ADDITIONthe residue is added to water
3. 3
   workup.STIRRINGshaken out with ethyl acetate
4. 4
   WaschenThe organic phase is washed three times with water
5. 5
   Trocknenonce with saturated common salt solution, dried with sodium sulfate
6. 6
   Einengenconcentrated by evaporation
7. 7
   SonstigeThe crude product is chromatographed on silica gel with hexane/10-25% ethyl acetate

Vorschrift

5.2 g of palladium(II) acetate, 77.8 g of potassium carbonate and 72.5 g of tetrabutylammonium bromide are added to a solution of 70 g of 3-benzyloxy-2-iodopyridine and 39.8 ml of acrylic acid methyl ester in 120 ml of dimethylformamide, and the suspension is stirred under argon atmosphere for 10 hours at 100° C. (bath temperature). The reaction mixture is concentrated by evaporation in a vacuum, the residue is added to water and shaken out with ethyl acetate. The organic phase is washed three times with water and once with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation. The crude product is chromatographed on silica gel with hexane/10-25% ethyl acetate. 48.2 g of 3-(3-benzyloxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester is obtained as oil.

Quelle