反応 #47533

反応方程式

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

収率 39.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度the reaction mixture was heated
2. 2
   温度to reflux for 0.75 h
3. 3
   温度The reaction mixture was refluxed for an additional 3 h
4. 4
   濃縮After this time, the mixture was concentrated in vacuo
5. 5
   workup.ADDITIONthe residue was diluted with water
6. 6
   抽出extracted with diethyl ether
7. 7
   洗浄The organic layer was then washed with 5% aqueous sodium hydroxide solution
8. 8
   乾燥dried over sodium sulfate
9. 9
   濃縮concentrated in vacuo

実験手順

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.

出典