반응 #71125

반응 방정식

3-bromo-2-oxo-propionic acid ethyl ester

trifluoroacetic anhydride

Na2CO3

N2

3-Bromo-2-oxo-propionic acid ethyl ester

3-phenyl-acrylamide

NaHCO3

→

title compound

(E)-2-Styryl-oxazole-4-carboxylic acid ethyl ester

용매

THF

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도at reflux for 15 h
3. 3
   온도at reflux for 15 h
4. 4
   여과The reaction mixture was then filtered over celite
5. 5
   기타the solvents were evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in THF (30 mL)
7. 7
   workup.ADDITIONtreated at 0° C.
8. 8
   workup.STIRRINGThe reaction mixture was then stirred at rt overnight
9. 9
   추출the mixture was extracted with EA (3×150 mL)
10. 10
    건조dried over MgSO4
11. 11
    여과filtered
12. 12
    기타the solvent was removed under reduced pressure
13. 13
    기타Purification of the residue by FC (1:9 EA-Hept)

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 3-phenyl-acrylamide (10.31 g, 67.95 mmol) and NaHCO3 (28.47 g, 339.73 mmol) in THF (260 mL) was treated with 3-bromo-2-oxo-propionic acid ethyl ester (13.04 mL, 88.33 mmol) and the reaction mixture was heated at reflux for 15 h. 3-Bromo-2-oxo-propionic acid ethyl ester (13.04 mL, 88.33 mmol) was added again and the reaction mixture was stirred at reflux for 15 h. The reaction mixture was then filtered over celite and the solvents were evaporated under reduced pressure. The residue was dissolved in THF (30 mL) and treated at 0° C., dropwise, with trifluoroacetic anhydride (30.0 mL, 215.83 mmol). The reaction mixture was then stirred at rt overnight. Sat. aq. Na2CO3 was added and the mixture was extracted with EA (3×150 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1:9 EA-Hept) gave the title compound as a yellow solid. TLC:rf (1:9 EA-Hept)=0.1. LC-MS-conditions 02: tR=1.01 min; [M+H]+=244.48.

출처