Hydrochloric Acid → HCID 118106659, compound

Participants

Reaction Steps

3.2 g (14.02 mmol) of diethyl 3-cyclopropylpentanedioate were dissolved in 24.7 ml of abs. THF, and, after cooling to −10° C., 25.2 ml (25.2 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. The reaction mixture was stirred at RT overnight. After cooling to 0° C., 100 ml of isopropanol were carefully added dropwise. The mixture was acidified by addition of 1 N hydrochloric acid and mixed with Celite. After filtration through Celite and washing with ethyl acetate and water, the filtrate was saturated with sodium chloride and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→2:1). This gave 1.35 g of the target product (66.8% of theory).

Provenance & Evidence