Reaktion #47651

Reaktionsgleichung

3-(2-hydroxy-2-methyl-propyl)-phenol

ethyl-2-butynoate

potassium carbonate

→

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

Ausbeute 84.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then cooled
2. 2
   Filtrationfiltered
3. 3
   WaschenThe solids were washed with a small amount of tetrahydrofuran
4. 4
   Sonstigethe combined filtrate was collected
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes)

Vorschrift

A mixture of 3-(2-hydroxy-2-methyl-propyl)-phenol (1.00 g, 6.01 mmol), ethyl-2-butynoate (4.00 g, 36.06 mol) and potassium carbonate (0.830 g, 6.01 mmol) in tetrahydrofuran (20 mL) in a sealed tube was heated to 80° C. for 3.75 h. The reaction mixture was then cooled and filtered. The solids were washed with a small amount of tetrahydrofuran and the combined filtrate was collected and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) to afford (E)-3-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester (1.41 g, 84%) as a colorless oil.

Quelle