تفاعل #85151

معادلة التفاعل

sodium hydride

3-ethyloxetane-3-carbaldehyde

tert-butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

→

tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate

المذيبات

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction was terminated by addition of 10 ml of saturated aqueous ammonium chloride solution
2. 2
   استخلاصthe reaction mixture was then extracted three times with 20 ml of ethyl acetate
3. 3
   تجفيفThe combined organic phases were dried over magnesium sulphate
4. 4
   ترشيحfiltered
5. 5
   أخرىthe solvent was removed under reduced pressure
6. 6
   أخرىThe residue was purified by flash chromatography (24 g cartridge, 35 ml/min, cyclohexane/ethyl acetate gradient)

الإجراء التجريبي

38.4 mg (1.60 mmol, 2 eq., 60% in mineral oil) of sodium hydride and 457 mg (4.00 mmol) of 3-ethyloxetane-3-carbaldehyde in 1 ml of dimethylformamide were added in succession to a solution of 300 mg (800 μmol) of tert-butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in 8 ml of dimethylformamide. After 15 min at RT, the reaction was terminated by addition of 10 ml of saturated aqueous ammonium chloride solution and the reaction mixture was then extracted three times with 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (24 g cartridge, 35 ml/min, cyclohexane/ethyl acetate gradient). Yield: 320 mg (82% of theory)

المصدر