Reaktion #303555

Reaktionsgleichung

ethyl bromo(difluoro)acetate

1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

samarium diiodide

→

ethyl 2,2-difluoro-3-[4-(5-fluoropyridin-2-yl)phenyl]-3-hydroxybutanoate

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was cooled
2. 2
   Sonstigequenched with 1N aqueous hydrochloric acid
3. 3
   SonstigeVolatiles were removed in vacuo
4. 4
   Sonstigethe residue was partitioned between ethyl acetate and 1 N hydrochloric acid
5. 5
   WaschenThe organic phase was washed with saturated aqueous sodium bicarbonate and brine
6. 6
   Trocknendried (sodium sulfate)
7. 7
   Einengenconcentrated in vacuo

Vorschrift

A solution of ethyl bromo(difluoro)acetate (0.53 mL, 4.1 mmol) and 1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone (800 mg, 3.7 mmol) in tetrahydrofuran (40 mL) was added to a 0.1 M solution of samarium diiodide in tetrahydrofuran (82 mL, 8.2 mmol) at ambient temperature. After stirring at ambient temperature for 3 min, the reaction was cooled and quenched with 1N aqueous hydrochloric acid. Volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic phase was washed with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-40% ethyl acetate/hexane afforded ethyl 2,2-difluoro-3-[4-(5-fluoropyridin-2-yl)phenyl]-3-hydroxybutanoate.

Quelle