Reaktion #463243

Reaktionsgleichung

4-hydroxy-3-methoxy-N,N-bis(1-methylethyl)benzenecarboxamide

cesium carbonate

ethyl 4-[5-bromopentoxy]benzenecarboximidoate

→

ethyl 4-[5-[2-methoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentoxy]benzenecarboximidoate

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Sonstigethe reaction is partitioned between ethyl acetate and water
3. 3
   Waschenthe organics washed with brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigeto afford a yellow oil
7. 7
   SonstigeThis material is purified by chromatography on silica gel (22 g) with 30-75% ethyl acetate/hexanes as the eluent

Vorschrift

A stirred solution of 4-hydroxy-3-methoxy-N,N-bis(1-methylethyl)benzenecarboxamide (319 mg, 1.27 mmol) in 3.5 mL anhydrous N,N-dimethylformamide is treated with cesium carbonate (435 mg, 1.33 mmol) and ethyl 4-[5-bromopentoxy]benzenecarboximidoate (400 mg, 1.27 mmol) and heated at 70° C. for 1.0 hours. After cooling to room temperature, the reaction is partitioned between ethyl acetate and water and the organics washed with brine, dried over sodium sulfate and concentrated in vacuo to afford a yellow oil. This material is purified by chromatography on silica gel (22 g) with 30-75% ethyl acetate/hexanes as the eluent to afford ethyl 4-[5-[2-methoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentoxy]benzenecarboximidoate as a colorless oil.

Quelle