Reaktion #52296

Reaktionsgleichung

triethylamine

Triflic anhydride

triphenylphosphine oxide

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

→

naphthalene-2-yl-propynoic acid ethyl ester

Ausbeute 42.7%

Lösungsmittel

1,2-dichloroethane

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturthe reaction mixture was heated
3. 3
   Temperaturat reflux for 1 hr
4. 4
   Waschenwashed with water
5. 5
   Trocknendried (MgSO4)
6. 6
   SonstigeThe solvent was removed under reduced pressure
7. 7
   Sonstigethe product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1)

Vorschrift

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).

Quelle