반응 #47420

반응 방정식

2-fluoro-3-methyl-phenol

ethyl-2-butynoate

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

→

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

수율 23.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   온도at reflux overnight
3. 3
   기타was removed in vacuo
4. 4
   workup.ADDITIONthe residue was diluted in diethyl ether
5. 5
   세척washed first with 1N aqueous hydrochloric acid
6. 6
   건조10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate
7. 7
   여과The mixture was filtered
8. 8
   기타evaporated
9. 9
   기타residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 330 g, 0% to 15% ethyl acetate/hexanes) which

실험 절차

To a stirred mixture of 2-fluoro-3-methyl-phenol (20.0 g, 0.158 mol) and ethyl-2-butynoate (33.6 g, 0.300 mol) in tetrahydrofuran (100 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (25.4 g, 0.167 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 residue purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 330 g, 0% to 15% ethyl acetate/hexanes) which afforded (E)-3-(2-fluoro-3-methyl-phenoxy)-but-2-enoic acid ethyl ester (8.40 g, 23%) as a clear oil.

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