تفاعل #1131941

معادلة التفاعل

N2

NH3

alpha-methylcinnamic acid

Et3N

ethyl chloroformate

→

title compound

(E)-2-Methyl-3-phenylacrylamide

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was vigorously stirred at 0° C. for 30 min and at rt for 1 h30
2. 2
   أخرىThe layers were then separated
3. 3
   استخلاصthe aq. layer extracted with CH2Cl2 (2×)
4. 4
   تركيزthe combined organic extracts were concentrated under reduced pressure
5. 5
   أخرىThe residue was partitioned between water and CH2Cl2
6. 6
   أخرىthe layers separated
7. 7
   استخلاصthe aq. layer extracted with CH2Cl2 (2×)
8. 8
   تجفيفextracts were dried (MgSO4)
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated under reduced pressure

الإجراء التجريبي

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of alpha-methylcinnamic acid (19.0 g, 116 mmol) and Et3N (17.1 mL, 122 mmol) in dry THF (500 mL) was treated with ethyl chloroformate (11.4 mL, 117 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 min then aq. NH3 (250 mL) in THF (150 mL) was added. The reaction mixture was vigorously stirred at 0° C. for 30 min and at rt for 1 h30. The layers were then separated, the aq. layer extracted with CH2Cl2 (2×) and the combined organic extracts were concentrated under reduced pressure. The residue was partitioned between water and CH2Cl2, the layers separated and the aq. layer extracted with CH2Cl2 (2×). The combined org. extracts were dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound as a white solid. LC-MS-conditions 01: tR=0.75 min; [M+H]+=162.07.

المصدر