Diisopropylamine → HCID 90014806, compound

Participants

Reaction Conditions

Reaction Steps

29.1 ml (72.8 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to −40° C., of 10.2 ml (72.8 mmol) of diisopropylamine in 35 ml of abs. THF. After the end of the addition, the mixture was stirred at −40° C. for another 30 min and then cooled to −78° C., and a solution of 7.1 ml (72.8 mmol) of ethyl acetate in 10 ml of abs. THF was added dropwise. The reaction mixture was stirred at −78° C. for 30 min, and a solution of 8.50 g (60.54 mmol) of ethyl 3-cyclopropylacrylate in a little THF was then added dropwise. After 1 h at −78° C., the mixture was slowly warmed to −40° C., then to 0° C., and a saturated aqueous ammonium chloride solution was finally added. After extraction with ethyl acetate, the organic phase was washed with 1 N hydrochloric acid and sat. sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 30:1→6:1). This gave 3.28 g of the target product (23.7% of theory).

Provenance & Evidence