反応 #47430

反応方程式

3-hydroxy-benzonitrile

methyl-2-butynoate

1,8-diazabicyclo[5.4.0]undec-7-ene

→

(E)-3-(3-cyano-phenoxy)-but-2-enoic acid methyl ester

収率 76.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   温度at reflux for 6 h
3. 3
   その他was removed in vacuo
4. 4
   workup.ADDITIONthe residue was diluted in diethyl ether
5. 5
   洗浄washed first with 1N aqueous hydrochloric acid
6. 6
   乾燥10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate
7. 7
   ろ過The mixture was filtered
8. 8
   その他evaporated
9. 9
   その他the residue dried under high vacuum which

実験手順

To a stirred mixture of 3-hydroxy-benzonitrile (3.30 g, 0.028 mol) and methyl-2-butynoate (5.40 g, 0.055 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.20 g, 0.028 mol) slowly. After addition was complete the mixture was stirred at reflux for 6 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue dried under high vacuum which afforded (E)-3-(3-cyano-phenoxy)-but-2-enoic acid methyl ester as an oil (4.60 g, 76%) and used without further purification.

出典