Reaktion #47658

Reaktionsgleichung

4-(2-hydroxy-2-methyl-propyl)-phenol

ethyl-2-butynoate

potassium carbonate

→

(E)-3-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester

Ausbeute 81.6%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then cooled to room temperature
2. 2
   SonstigeThe solids were isolated by filtration
3. 3
   Waschenwashed with a small amount of tetrahydrofuran
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   Sonstigethe residue was purified by flash chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which

Vorschrift

To a stirred mixture of 4-(2-hydroxy-2-methyl-propyl)-phenol (0.850 g, 5.11 mmol) and ethyl-2-butynoate (3.45 g, 30.66 mmol) in tetrahydrofuran (20 mL) was added potassium carbonate (0.710 g, 5.11 mmol). The mixture was heated in a sealed tube at 80° C. for 5.5 h. The reaction mixture was then cooled to room temperature. The solids were isolated by filtration and washed with a small amount of tetrahydrofuran. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which afforded (E)-3-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester (1.16 g, 81%) as a viscous colorless oil.

Quelle