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

Participants

Reaction Conditions

Reaction Steps

Under argon, 1.19 g (29.64 mmol, 60% pure) of sodium hydride were suspended in 25 ml of toluene and 25 ml of THF, and the suspension 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 reaction mixture was then warmed to room temperature. The mixture was stirred at room temperature for 2 hours, and 50 ml of water were then added. After removal of the organic phase, the aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulfate. 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