Sodium Chloride → HCID 58136329, compound

Participants

Reaction Steps

At RT and with slight cooling, 99.23 g (394 mmol) of tert-butyl diethylphosphonoacetate were added dropwise to a suspension of 15.74 g (394 mmol) of sodium hydride (60% in mineral oil) in 540 ml of THF. After the addition had ended, the mixture was stirred at RT for 30 min and, after cooling to 0° C., a solution of 60.5 g (358 mmol) of 4-fluoro-3-nitrobenzaldehyde in 324 ml of THF was added. The reaction mixture was stirred at RT overnight and then added to a 10% strength aqueous sodium chloride solution. The mixture was extracted twice with ethyl acetate. The combined organic phases were washed with sat. sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography (twice) on silica gel (mobile phase petroleum ether/ethyl acetate 9:1). This gave 82.0 g (84.9% of theory) of the target product.

Provenance & Evidence