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

Temperature

-78 °C

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%).

1. stirringat −78° C., and the resulting mixture was stirred under a nitrogen atmosphere at −78° C. for 30 minutes
2. extractionthe organic matter was extracted with ethyl acetate
3. washThe organic layer was washed with water
4. dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
7. customwas obtained
8. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 20:80 (v/v)), whereby the objective title compound
9. customwas obtained as a colorless oily substance (4.31 g, yield: 54%)

ORD record

ord-ed24bddf58bf40189d3bc5354e0e14a0

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222281B2