Reacción #52296

Ecuación de reacción

triethylamine

Triflic anhydride

triphenylphosphine oxide

3-naphthalen-2-yl-3-oxo-propionic acid ethyl ester

→

naphthalene-2-yl-propynoic acid ethyl ester

Rendimiento 42.7%

Disolventes

1,2-dichloroethane

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturathe reaction mixture was heated
3. 3
   Temperaturaat reflux for 1 hr
4. 4
   Lavadowashed with water
5. 5
   Secadodried (MgSO4)
6. 6
   OtroThe solvent was removed under reduced pressure
7. 7
   Otrothe product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1)

Procedimiento

Triflic anhydride (2.9 mL, 17 mmol) was added dropwise to a solution of triphenylphosphine oxide (4.8 g, 17 mmol) in 1,2-dichloroethane (40 mL) at 0° C. The resulting suspension was stirred for 15 minutes, followed by the dropwise addition of a solution of 3-naphthalen-2-yl-3-oxo-propionic acid ethyl ester (3.2 g, 12 mmol) in 1,2-dichloroethane (40 mL). After the addition was complete, triethylamine (4.0 mL, 29 mmol) was added and the reaction mixture was heated at reflux for 1 hr. The solution was cooled to room temperature, washed with water, and dried (MgSO4). The solvent was removed under reduced pressure, and the product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1) to yield naphthalene-2-yl-propynoic acid ethyl ester (1.15 g, 37% yield) as a yellow oil. 1H NMR (CDCl3) δ 8.25 (s, 1H), 7.95 (m, 3H), 7.66 (m, 3H), 4.46 (m, 2H), 1.51 (t, 3H, J=8.0 Hz).

Fuente