Journal of Organic Chemistry p. 1713 - 1718 (1991)
Update date:2022-08-17
Topics:
Witzeman, J. Stewart
Nottingham, W. Dell
Reaction of various nucleophiles with tert-butyl acetoacetate (t-BAA, 1a) is shown to be a convenient method for the preparation of a wide variety of acetoacetic acid derivatives.This material can be used to prepare acetoacetates and acetoacetamides from a wide variety of alcohols and amines.Reaction of 1a with an unhindered primary amine such as n-heptylamine under standard conditions gives unwanted byproducts due to the formation of the enamines 24 and 25.Formation of these byproducts can be minimized by dilution and/or altering the mode of addition.
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