Reaktion #171464

Reaktionsgleichung

Cesium carbonate

4-phenylpyridin-2-ol

ethyl 4-bromo-2-ethyl-2-(methylsulfonyl)butanoate

→

oil

Ausbeute 20.0%

Ethyl 2-ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanoate

Ausbeute 20.0%

Lösungsmittel

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through a pad of Celite
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigeThe crude material was purified by flash chromatography on silica gel (4:1-0:1 heptane/ethyl acetate)

Vorschrift

Cesium carbonate (0.71 g, 2.2 mmol, 4.0 equiv) was added to a solution of the 4-phenylpyridin-2-ol (0.10 g, 0.58 mmol, 1.05 equiv) and ethyl 4-bromo-2-ethyl-2-(methylsulfonyl)butanoate (0.17 g, 0.55 mmol, 1.0 equiv) in tetrahydrofuran (5 mL). The resulting mixture was heated to 55° C. and allowed to stir for 3 days. The reaction was diluted with ethyl acetate (20 mL), filtered through a pad of Celite, and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (4:1-0:1 heptane/ethyl acetate) to provide a light yellow oil (43 mg, 20%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.15 (t, J=7.42 Hz, 3 H) 1.33 (t, J=7.13 Hz, 3 H) 2.07-2.19 (m, 1 H) 2.26-2.36 (m, 1 H) 2.44 (ddd, J=14.89, 11.18, 4.98 Hz, 1 H) 2.59-2.71 (m, 1 H) 3.15 (s, 3 H) 4.19-4.37 (m, 4 H) 6.45 (dd, J=7.03, 1.56 Hz, 1 H) 6.72-6.78 (m, 1 H) 7.38-7.48 (m, 4 H) 7.53-7.60 (m, 2 H).

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