4-Nitrobenzaldehyde → Ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate

Participants

Reaction Conditions

Reaction Steps

Ethyl acetate (3.55 g, 40.3 mmol) was dissolved in tetrahydrofuran (100 mL), and a 1 M lithium bis(trimethylsilyl)amide hexane solution (40.0 mL, 40.0 mmol) was added thereto at −78° C., and then, the resulting mixture was stirred under a nitrogen atmosphere at −78° C. for 20 minutes. Thereafter, a tetrahydrofuran solution of 4-nitrobenzaldehyde (5.08 g, 33.6 mmol) was added thereto at −78° C., and the resulting mixture was stirred under a nitrogen atmosphere at −78° C. for 30 minutes. To the reaction solution, a saturated aqueous solution of ammonium chloride was added at −78° C., and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 20:80 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (4.31 g, yield: 54%).

Provenance & Evidence