Ethyl isobutyrate → HCID 11009344, compound

Participants

Reaction Conditions

Reaction Steps

To dehydrated THF (20 mL) was added a 2.0M LDA/THF-ethylbenzene-heptane solution (7.88 mL), this was cooled to around −78° C. in a dry ice-methanol bath, and a solution of ethyl 2-methylpropanoate (1.74 g) in dehydrated THF (5 mL) was slowly added dropwise. After the mixture was stirred at around −78° C. for 1 hour, this solution was added dropwise to a suspension of succinic acid anhydride (1.50 g) in dehydrated THF (5 mL) over 5 minutes under an ice bath. After stirred at the same temperature for 40 minutes, the mixture was stirred at room temperature for 3 hours. Into the reaction solution was slowly placed water under an ice bath, ethyl acetate and an aqueous saturated sodium bicarbonate solution were added, followed by extraction. To the resulting aqueous phase was added 1N hydrochloric acid to adjust a pH at around 3, followed by extraction with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was washed with dichloromethane, a compound derived from succinic acid anhydride was removed by filtration, and the resulting filtrate was concentrated under reduced pressure to obtain the title compound (2.22 g) having the following physical property values.

Provenance & Evidence