Diisopropylamine → HCID 14223731, compound

Participants

Reaction Steps

To a solution of lithium diisopropylamide prepared from diisopropylamine (27.3 g) and n-butyl lithium (161.75 ml, 1.6M) in tetrahydrofuran (700 ml), was added a solution of (-)-methyl methoxyphenyl sulfoxide (20 g) in tetrahydrofuran (40 ml) at -20° C. After 15 minutes, ethyl acetate (22.8 g) was added and the mixture was allowed to reach room temperature. After quenching with NaH2PO4, the solvent was removed in vacuo and the residue was extracted with ether. The extract was purified by chromatography on silica gel (1:1 acetone/hexane) to give (-)-4-methoxyphenylsulfinylacetone, m.p. 56°-58° C., [α]D =-149.8° (C=0.032, methanol).

Provenance & Evidence