تفاعل #2467968

معادلة التفاعل

methyl 4-hydroxy-5-(methoxycarbonyl)-3-nitrothiophene-2-carboxylate

potassium carbonate

Dimethyl sulfate

→

solid

المردود 45.0%

Methyl 4-methoxy-5-(methoxycarbonyl)-3-nitrothiophene-2-carboxylate

المردود 45.0%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added to the above reaction mixture slowly
2. 2
   workup.ADDITIONa catalytic amount of KI was added
3. 3
   درجة الحرارةThe mixture was refluxed for 4 h
4. 4
   أخرىthe cooled reaction mixture
5. 5
   ترشيحwas filtered
6. 6
   غسيلthe solids were washed with acetone
7. 7
   أخرىAcetone was removed under reduced pressure
8. 8
   أخرىthe residue was chromatographed over silica gel column

الإجراء التجريبي

To a solution of methyl 4-hydroxy-5-(methoxycarbonyl)-3-nitrothiophene-2-carboxylate (650 mg, 2.5 mmol) in acetone (20 mL) was added potassium carbonate (0.68 g, 5 mmol) at it Dimethyl sulfate (0.36 mL, 3.73 mmol) was added to the above reaction mixture slowly with stirring and a catalytic amount of KI was added. The mixture was refluxed for 4 h and the cooled reaction mixture was filtered and the solids were washed with acetone. Acetone was removed under reduced pressure and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10) as eluents to give the product as a pale yellow color solid (0.3 g, 45%), mp 80-82° C. 1H NMR (400 MHz, CDCl3): δ 4.08 (3H, s), 3.94 (3H, s), 3.92 (3H, s).

المصدر