반응 #311835

반응 방정식

Alanine ethyl ester hydrochloride

Acetonylacetone

sodium acetate

→

ethyl 2-(2,5-dimethylpyrrol-1-yl)propionate

수율 59.0%

용매

acetic acid

반응 조건

후처리

1. 1
   온도the mixture heated
2. 2
   온도under reflux for 5 hours
3. 3
   workup.DISTILLATIONThe acetic acid was distilled off under reduced pressure, and ethyl acetate
4. 4
   workup.ADDITIONadded to the residue
5. 5
   세척The organic layer was washed with an aqueous solution of sodium hydrogen carbonate
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타to afford 29.2 g of a crude product
9. 9
   기타The product was chromatographed on a column of silica gel

실험 절차

Alanine ethyl ester hydrochloride (30.8g; 0.2 mole) was dissolved in 100 ml of acetic acid. Acetonylacetone (22.8 g; 0.2 mole) and then 16.4 g (0.2 mole) of sodium acetate were added to the solution, and the mixture heated under reflux for 5 hours. The acetic acid was distilled off under reduced pressure, and ethyl acetate added to the residue. The organic layer was washed with an aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 29.2 g of a crude product. The product was chromatographed on a column of silica gel using cyclohexane/ethyl acetate (4/1) as an eluent to afford ethyl 2-(2,5-dimethylpyrrol-1-yl)propionate (23.0 g, 0.118 mole, 59.0%).

출처