Sodium Chloride → (RS)-6-methoxy-2-(2-oxopropyl)-1-indanone

Participants

Reaction Steps

A solution of LDA, prepared at 0° from 3.12 ml of diisopropyl-amine and 13.8 ml of n-butyllithium (1.6N in hexane), in 40 ml of anhydrous tetrahydrofuran was added dropwise while stirring during 10 minutes to a solution, cooled to -70°, of 2.96 g of 6-methoxy-1-indanone in 300 ml of anhydrous tetrahydrofuran. After 15 minutes, a solution of 1.62 ml of chloroacetone in 40 ml of anhydrous tetrahydrofuran was added dropwise to the solution during 5 minutes and the mixture was subsequently stirred at room temperature for 2 hours. The reaction mixture was poured on to 150 ml of ice Thereafter 150 ml of saturated sodium chloride solution were added and the mixture was extracted twice with 300 ml of diethyl ether each time. The combined organic phases were washed once with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated in a vacuum. The crude product obtained was purified by column chromatography on silica gel (hexane/diethyl ether 3:2, then 2:3). 1.8 g (45%) of (RS)-6-methoxy-2-(2-oxopropyl)-1-indanone were obtained as a red oil.

Provenance & Evidence