Reaktion #357259

Reaktionsgleichung

N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide

(2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate

Cs2CO3

→

subtitled compound

Ausbeute 42.6%

N-[2-[(2S)-Oxiran-2-ylmethoxy]-5-(trifluoromethyl)phenyl]acetamide

Ausbeute 42.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between ethyl acetate and water
2. 2
   TrocknenThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether)

Vorschrift

A mixture of N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide (282 mg, 1.28 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (331.5 mg, 1.28 mmol) and Cs2CO3 (487.5 mg, 1.28 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether) to give the subtitled compound (150 mg).

Quelle