反応 #47410

反応方程式

2-fluoro-3-methoxy-phenol

methyl-2-butynoate

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

→

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

収率 67.4%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   温度at reflux overnight
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 2-fluoro-3-methoxy-phenol (3.88 g, 0.027 mol) and methyl-2-butynoate (5.97 g, 0.061 mol) in tetrahydrofuran (30 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.64 g, 0.030 mol) slowly. After addition was complete the mixture was stirred at reflux overnight. 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-(2-fluoro-3-methoxy-phenoxy)-but-2-enoic acid methyl ester (4.37 g, 63%) as a colorless oil and used without further purification.

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