Diisopropylamine → HCID 58136634, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 11.7 ml (83.32 mmol) of diisopropylamine were dissolved in 200 ml of THF and cooled to −78° C. 33.3 ml (83.32 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to this solution. The reaction solution was then warmed to −10° C. and stirred at this temperature for 10 min. The reaction solution was then once more cooled to −78° C., and 8.4 ml (72.9 mmol) of methyl 2-methylpropanoate were added slowly. The mixture was then stirred at −78° C. for 30 min. 15 g (69.4 mmol) of 1-(bromomethyl)-3-nitrobenzene, dissolved in 150 ml of THF, were then slowly added dropwise. After the addition had ended, the solution was slowly warmed to room temperature and stirred overnight. After TLC check (mobile phase: toluene/ethyl acetate 10:1), saturated ammonium chloride solution was added and the reaction mixture was taken up in ethyl acetate. The aqueous phase was extracted three 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 toluene/ethyl acetate 20:1). This gave 12.2 g (51.4 mmol, 74% of theory) of the title compound.

Provenance & Evidence