Reaktion #49529

Reaktionsgleichung

hydrochloric acid

4-Formyl-3-methoxymethoxybenzoic acid

EDCI

HOBT monohydrate

cumylamine

→

4-formyl-3-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide

Ausbeute 78.1%

Lösungsmittel

water

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature for 1 hour
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with water and saturated aqueous sodium hydrogencarbonate solution and saturated brine
4. 4
   Trocknenby drying over anhydrous sodium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30)

Vorschrift

4-Formyl-3-methoxymethoxybenzoic acid (2.57 g, 12.2 mmol) was dissolved in DMF (50 mL), and the solution was added with EDCI (4.68 g, 24.4 mmol), HOBT monohydrate (1.65 g, 12.2 mmol) and cumylamine (4.03 mL, 24.4 mmol), followed by stirring at room temperature for 4 hours. The reaction mixture was added with water (10 mL) and 1 mol/L hydrochloric acid (10 mL) and stirred at room temperature for 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30) to obtain 4-formyl-3-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide (3.12 g, yield 78%).

Quelle