반응 #52296

반응 방정식

triethylamine

Triflic anhydride

triphenylphosphine oxide

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

→

naphthalene-2-yl-propynoic acid ethyl ester

수율 42.7%

용매

1,2-dichloroethane

1,2-dichloroethane

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   온도the reaction mixture was heated
3. 3
   온도at reflux for 1 hr
4. 4
   세척washed with water
5. 5
   건조dried (MgSO4)
6. 6
   기타The solvent was removed under reduced pressure
7. 7
   기타the product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1)

실험 절차

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).

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