تفاعل #70737

معادلة التفاعل

t-BuOK

t-BuOK

cyanoacetamide

(3E)-3-hepten-2-one

→

6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinecarbonitrile

المردود 32.0%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   workup.WAITthe reaction mixture was placed under an atmosphere of oxygen for an additional 1 h
2. 2
   أخرىThe reaction mixture was purged with argon
3. 3
   workup.ADDITIONdiluted with 4 volumes of H2O
4. 4
   workup.ADDITION5 volumes of 4 N HCl, which were added slowly
5. 5
   ترشيحThe reaction mixture was filtered
6. 6
   غسيلwashed with water
7. 7
   أخرىdried

الإجراء التجريبي

To a solution of DMSO (300 mL) containing t-BuOK (20 g, 178 mmol) and cyanoacetamide (16.5 g, 196 mmol) was added (3E)-3-hepten-2-one (20 g, 178 mmol), and the contents were stirred at room temperature for 30 min. Additional t-BuOK (60 g, 534 mmol) was added and the reaction mixture was placed under an atmosphere of oxygen for an additional 1 h. The reaction mixture was purged with argon, diluted with 4 volumes of H2O, and then 5 volumes of 4 N HCl, which were added slowly. The reaction mixture was filtered, washed with water, and dried to give 6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinecarbonitrile (10 g, 32%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.25-12.40 (br s, 1H), 6.18 (s, 1H), 2.53 (t, 2H), 2.22 (s, 3H), 1.57-1.64 (m, 2H), 0.84 (t, 3H).

المصدر