Reaktion #357287

Reaktionsgleichung

methyl 4-fluoro-2-hydroxybenzoate

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

Cs2CO3

→

subtitled compound

Ausbeute 96.7%

Methyl 4-fluoro-2-[(2S)-oxiran-2-ylmethoxy]benzoate

Ausbeute 96.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between ethyl acetate and H2O, organic layer
2. 2
   Trocknenwas dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo

Vorschrift

A mixture of methyl 4-fluoro-2-hydroxybenzoate (456.3 mg, 1.76 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (300 mg, 1.76 mmol) and Cs2CO3 (687.4 mg, 2.11 mmol) in DMF (4.5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O, organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was opurified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit) to give the subtitled compound (385 mg).

Quelle