Hydrochloric Acid → Ethyl 6-acetoxy-2,2-dimethylhexanoate

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (8.25 ml) was dissolved in anhydrous tetrahydrofuran (100 ml) under an argon atmosphere, and the solution was cooled at -70° C. 1.6M n-butyllithium hexane solution (37 ml, 60 mmole) was added dropwise to the solution, to which a solution of ethyl isobutyrate (5.6 g, 48 mmole) in anhydrous tetrahydrofuran (5 ml) was then added, while maintaining the reaction temperature at not higher than -60° C. After stirring was continued for 30 minutes under the same reaction conditions, a solution of 4-acetoxybutyl iodide (12 g, 50 mmole) in hexamethylphosphortriamide (5 ml) was added dropwise to the reaction solution, and the reaction was allowed to proceed until the mixture rose to room temperature. After the completion of the reaction, 2N hydrochloric acid (10 ml) was added, and the mixture was concentrated under reduced pressure. The resulting product was dissolved in ethyl acetate (100 ml), and the organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel using isopropyl ether to give ethyl 6-acetoxy-2,2-dimethylhexanoate (5.6 g, 50%).

Provenance & Evidence