Reaktion #85496

Reaktionsgleichung

N-benzyl-2-chloro-N-methylacetamide

5-(tetradecyloxy)furan-2-carboxylic acid

tetrabutylammonium hydroxide pentahydrate

sodium iodide

→

desired compound

2-(benzyl(methyl)amino)-2-oxoethyl 5-(tetradecyloxy)furan-2-carboxylate

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with brine (5 mL), water (5 mL) and EtOAc (40 mL)
2. 2
   SonstigeThe phases were separated
3. 3
   workup.ADDITIONthe organic phase was further diluted with EtOAc (30 mL)
4. 4
   Waschenwashed successively with water (30 mL) and brine (30 mL)
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe resulting crude material was purified by flash chromatography
8. 8
   Wascheneluting with 5-20% EtOAc in hexanes

Vorschrift

The above prepared N-benzyl-2-chloro-N-methylacetamide (0.250 g) was dissolved in 10 mL of N,N-dimethylformamide. To this solution were added 5-(tetradecyloxy)furan-2-carboxylic acid (0.180 g, 0.544 mmol), tetrabutylammonium hydroxide pentahydrate (0.209 g, 0.554 mmol), and sodium iodide (˜15 mg). The suspension was heated to 60° C. with stirring for 14 hrs. The reaction was quenched with brine (5 mL), water (5 mL) and EtOAc (40 mL). The phases were separated and the organic phase was further diluted with EtOAc (30 mL), washed successively with water (30 mL) and brine (30 mL) and then dried and concentrated. The resulting crude material was purified by flash chromatography eluting with 5-20% EtOAc in hexanes to give the desired compound as a viscous oil. The material was further purified by recrystallization from 2-propanol and water to yield 0.130 g (52%) of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.20-7.40 (m, 6H), 5.30-5.35 (m, 1H), 4.92 (s, 2H), 4.50-4.61 (app d, 2H), 4.10 (m, 2H), 2.90-2.98 (app d, 3H), 1.79 (p, 2H), 1.18-1.50 (m, 22H), 0.89 (t, 3H).

Quelle