2-Methoxyallyl bromide. A superior acetonyl alkylating agent

RM Jacobson, RA Raths…

Index: Jacobson,R.M. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 15 p. 2545 - 2549

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Citation Number: 62

Abstract

Heating l-bromo-2, 2-dimethoxypropane (1) in the presence of a catalytic amount of diisopropylethylammonium p-toluenesulfonate (2) gives 3-bromo-2-methoxy-1-propene (3) in greatly improved yield. Bromide 3 is a good alkylating agent monoalkylating acids, nitriles, esters, ketones, dialkylamides, enamines, and imines in yields of 44-96%. Alkylation of the lithium salt of imines with 3 followed by hydrolysis leads to a-acetonyl ketones which can ...