Water → tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

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Reaction Conditions

Reaction Steps

Under argon, 1.19 g (29.64 mmol, 60%) of sodium hydride were suspended in 25 ml of toluene and 25 ml of THF, and the mixture was cooled to 0° C. 7.28 ml (30.99 mmol) of tert-butyl (diethoxyphosphoryl)acetate were then slowly added dropwise, and the mixture was stirred at 0° C. for 30 min. 5 g (26.94 mmol) of 4-chloro-3-nitrobenzaldehyde were then added to the reaction mixture, and the mixture was subsequently warmed to room temperature. The mixture was stirred at room temperature for 2 h, and 50 ml of water were then added. The organic phase was separated off, and the aqueous phase was then extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulphate. After filtration, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 9:1). This gave 6.77 g (23.86 mmol, 77% of theory) of the title compound.

Provenance & Evidence