Sodium Chloride → 7-benzyloxy-5-oxiranyl-1H-quinolin-2-one

Participants

Reaction Steps

6.0 g (18.3 mmol) 7-benzyloxy-5-(2-chloro-acetyl)-1H-quinolin-2-one are placed in 150 mL tetrahydrofuran and at 0 to 5° C. combined with 434 mg (819.9 mmol) lithium borohydride. The mixture is stirred for 30 minutes, then 43 mL of a 2.5 molar sodium hydroxide solution are added and the mixture is stirred for a further 4 hours with heating to ambient temperature. The mixture is combined with sodium chloride solution, filtered and extracted repeatedly with ethyl acetate/tetrahydrofuran (1:1). The solid filtered off and the organic phases are combined and freed from the solvent. The residue is suspended in methanol, suction filtered and dried. Yield 4.8 g (89%); mass spectroscopy: [M+H]+=294.

Provenance & Evidence