반응 #217747

반응 방정식

isobutyraldehyde

methyl-cyano-acetate

ammonium hydroxide

acetic acid

→

2-cyano-4-methyl-2-pentenoic acid methyl ester

수율 90.4%

2-Cyano-4-methyl-2-pentenoic acid methyl ester

수율 90.4%

용매

toluene

반응 조건

후처리

1. 1
   온도to reflux under a Dean-Stark trap for 12 hours
2. 2
   추출extracted with saturated NaHSO3 (3×100 mL), saturated NaHCO3 (3×100 mL), and 100 mL of brine
3. 3
   건조The organic layer is dried over Na2SO4
4. 4
   기타the solvent is evaporated
5. 5
   workup.DISTILLATIONThe remaining oil is distilled under high vacuum (0.5 mm Hg, B.P.=115-120° C.)

실험 절차

A solution of isobutyraldehyde (30.0 g, 416 mmol), methyl-cyano-acetate 5 (20.6 g, 208 mmol), ammonium hydroxide (3.2 g, 41.6 mmol) and acetic acid (5.0 g, 83.2 mmol) in 500 mL of toluene is warmed to reflux under a Dean-Stark trap for 12 hours. The mixture is cooled to room temperature and extracted with saturated NaHSO3 (3×100 mL), saturated NaHCO3 (3×100 mL), and 100 mL of brine. The organic layer is dried over Na2SO4, and the solvent is evaporated. The remaining oil is distilled under high vacuum (0.5 mm Hg, B.P.=115-120° C.) to give 28.8 g of 2-cyano-4-methyl-2-pentenoic acid methyl ester 61 as an oil (90% yield).

출처