Sodium Chloride → HCID 19036578, compound

A solution of LDA, prepared at 0° from 4.25 ml of diisopropyl-amine and 18.8 ml of N-butyllithium (1.6N in hexane), in 60 ml of anhydrous tetrahydrofuran, was added dropwise while stirring during 15 minutes to a solution, cooled to -70°, of 3.24 g of 5-methoxy-1-indanone in 350 ml of anhydrous tetrahydrofuran. After 45 minutes, a solution of 1.6 ml of chloroacetone in 60 ml of anhydrous tetra-hydrofuran was added dropwise to the solution during 15 minutes and the mixture was subsequently stirred at room temperature for 2 hours. The reaction mixture was poured on to 150 ml of ice, 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 3:7). 1.4 g (32%) of (RS)-5-methoxy-2-(2-oxopropyl)-1-indanone were obtained as a solid with m.p. 73°.

1. additionwas added dropwise
2. waitAfter 45 minutes
3. stirringthe mixture was subsequently stirred at room temperature for 2 hours
4. additionwere added
5. extractionthe mixture was extracted twice with 300 ml of diethyl ether each time
6. washThe combined organic phases were washed once with 200 ml of saturated sodium chloride solution
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in a vacuum
9. customThe crude product obtained
10. customwas purified by column chromatography on silica gel (hexane/diethyl ether 3:7)

ORD record

ord-b7c9a3eed3ca41f8aba028b4cc2c02e8

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05646173