Reacción #1747826

Ecuación de reacción

ethynylmagnesium bromide

3-ethoxy-2-cyclohexen-1-one

HCl

→

3-Ethynyl-2-cyclohexen-1-one

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 15 min the acidic phase
2. 2
   Extracciónwas extracted with dichloromethane (5×50 mL)
3. 3
   LavadoThe combined organic extracts were washed with water (2×50 mL)
4. 4
   Secadodried (MgSO4)
5. 5
   OtroEvaporation of the solvent
6. 6
   Otrogave an oil that
7. 7
   Otrowas purified by column chromatography (silica, ethyl acetate/hexane 1:9)
8. 8
   Otroto yield a yellow oil, 2.71 g, 22.6 mmol, 84%)

Procedimiento

To a solution of 0.5N ethynylmagnesium bromide in tetrahydrofuran (100 mL) was added under N2 and stirring 3-ethoxy-2-cyclohexen-1-one (3.75 g, 26.8 mmol) in tetrahydrofuran (12.5 mL). The mixture was stirred at RT for 20 h when it was acidified with 1N HCl (200 mL). After stirring for 15 min the acidic phase was extracted with dichloromethane (5×50 mL). The combined organic extracts were washed with water (2×50 mL) and dried (MgSO4). Evaporation of the solvent gave an oil that was purified by column chromatography (silica, ethyl acetate/hexane 1:9) to yield a yellow oil, 2.71 g, 22.6 mmol, 84%). Analysis were in agreement with literature data.

Fuente