Sodium hydride → Bis(1,1-dimethylethyl) [2-fluoro-3-(1-naphthalenyloxy)-4-nitrophenyl]propanedioate

Beteiligte Stoffe

Reaktionsschritte

Sodium hydride (60% oil dispersion) (4.07 g, 102 mmol) was added in portions to a solution of di-t-butyl malonate (11.01 g, 50.9 mmol) in THF (200 mL) at room temperature. After gas evolution ceased, 1-[(2,3-difluoro-6-nitrophenyl)oxy]naphthalene (13.94 g, 46.3 mmol), dissolved in THF (100 mL), was added. The reaction mixture was stirred at room temperature for 2 hrs and then poured on to ice and extracted with ethyl acetate. The organic layer was dried over sodium sulfate. The solvent was evaporated to give the title compound (26.59 g, 102%) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.33-8.44 (m, 1H), 7.83-7.95 (m, 2H), 7.51-7.65 (m, 4H), 7.23-7.34 (m, 1H), 6.60 (d, 1H), 4.82 (s, 1H), 1.49 (s, 18H). ESMS: m/z 497.

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