Tert-butyl acetoacetate → tert-butyl 2-hydroxyimino-3-oxobutanoate

Participants

Reaction Conditions

Reaction Steps

t-Butyl-3-oxobutyrate (158 g, 1 mol) was dissolved in 200 mL of acetic acid in a 500 mL 3-neck round bottom flask equipped with a thermometer, addition funnel and mechanical stirring. The mixture was cooled in an ice bath to about 10° C. Sodium nitrite (69 g, 1 mol) was added over 75 minutes keeping the temperature under 15° C. The cold bath was removed and the mixture stirred for 30 minutes and then allowed to stand for 3.5 hours to give t-butyl-2-hydroxyimino-3-oxobutyrate.

Provenance & Evidence