반응 #47533

반응 방정식

3-chloro-but-2-enoic acid ethyl ester

Potassium t-butoxide

3-bromo-phenol

→

(E)-3-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester

수율 39.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도to reflux for 0.75 h
3. 3
   온도The reaction mixture was refluxed for an additional 3 h
4. 4
   농축After this time, the mixture was concentrated in vacuo
5. 5
   workup.ADDITIONthe residue was diluted with water
6. 6
   추출extracted with diethyl ether
7. 7
   세척The organic layer was then washed with 5% aqueous sodium hydroxide solution
8. 8
   건조dried over sodium sulfate
9. 9
   농축concentrated in vacuo

실험 절차

Potassium t-butoxide (10.5 g, 0.094 mol) was added to a stirred solution of 3-bromo-phenol (8.18 g, 0.047 mol) in tetrahydrofuran (30 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191, 7.00 g, 0.047 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester (5.20 g, 39%) as a yellow oil.

출처