تفاعل #2430

معادلة التفاعل

Methyl(3-amino)benzoate

4-Pentenoyl chloride

4-pentenoic acid

thionyl chloride

→

oil

المردود 32.0%

Methyl 3-(4-pentenoylamino)benzoate

المردود 32.0%

المذيبات

pyridine

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىat 0° C
2. 2
   أخرىevaporated
3. 3
   أخرىazeotroped with DCM)
4. 4
   workup.ADDITIONwas added dropwise in DCM (3 ml)
5. 5
   أخرىThe mixture was evaporated
6. 6
   أخرىpartitioned between EtOAc and 1M HCl
7. 7
   غسيلThe organic portion was washed with 5% KHCO3 and brine
8. 8
   ترشيحfiltered (Whatman® 1PS, phase separator)
9. 9
   أخرىevaporated
10. 10
    أخرىThe residue was chromatographed (eluant 30% EtOAc in hexanes)

الإجراء التجريبي

Methyl(3-amino)benzoate (4.5 g, 29.8 mmol) was taken up in DCM (10 ml) and pyridine (1 ml) at 0° C. 4-Pentenoyl chloride (freshly prepared from 4-pentenoic acid (3.0 g, 29.97 mmol) and thionyl chloride (6.6 ml) at r.t. for 1 h, evaporated and azeotroped with DCM) was added dropwise in DCM (3 ml). The mixture was allowed to warm to r.t. and stirred overnight. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1PS, phase separator), and evaporated. The residue was chromatographed (eluant 30% EtOAc in hexanes) to provide a colourless oil (2.20 g, 32%).

المصدر