Sodium hydride → Benzyl 3-(2-cyano-3-nitrophenoxy)-2,2-dimethylpropanoate

Temperatur

0 °C

To a solution of benzyl 3-hydroxy-2,2-dimethylpropanoate (Yang, D. et al. J. Am. Chem. Soc. 2002, 124, 9966. 6.68 g, 32.1 mmol) in dry THF (200 mL) was carefully added NaH (60% in mineral oil, 3.5 g, 87.5 mmol) in small portions at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. under nitrogen for 2 hrs. To this solution was added 2,6-dinitrobenzonitrile (6.19 g, 32.1 mmol), and the reaction solution was stirred at 0° C.-RT under nitrogen overnight. The reaction mixture was quenched with brine, and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting (Elunet: 20% EtOAc in hexanes) to give the title compound as a brown solid (10.0 g, 87%). MS 355 (MH+).

1. customat 0° C.
2. stirringthe reaction solution was stirred at 0° C.-RT under nitrogen overnight
3. customThe reaction mixture was quenched with brine
4. extractionextracted with EtOAc (3×)
5. washThe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. customAfter evaporation of the solvent
8. customthe residue was purified by chromatography on silica gel eluting (Elunet: 20% EtOAc in hexanes)

ORD-Eintrag

ord-5f9ee585ed6e447fa3cddd8df43d3e57

Quelldatensatz

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08815956B2