تفاعل #970380

معادلة التفاعل

ammonium chloride

diethyl cyanomethylphosphonate

sodium hydride

2-methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

→

title compound

المردود 76.3%

(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrile

المردود 76.3%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   workup.STIRRINGthe mixture was further stirred for 1 hr
3. 3
   استخلاصthe mixture was extracted with ethyl acetate
4. 4
   غسيلThe extract was washed with saturated brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   أخرىThe solvent was evaporated under reduced pressure
7. 7
   أخرىthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

الإجراء التجريبي

To a suspension of 60% sodium hydride (90.0 mg, 2.24 mmol) in tetrahydrofuran (9 mL) was added diethyl cyanomethylphosphonate (393 μL, 2.43 mmol) under ice-cooling, and the mixture was stirred for 15 min. Thereto was added a solution of 2-methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one (350 mg, 1.87 mmol) in tetrahydrofuran (9 mL), and the mixture was further stirred for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (300 mg, yield 76%).

المصدر