New Reagent for Convenient Access to the α,β‐Unsaturated N ‐Methoxy‐ N ‐methyl‐amide Functionality by a Synthesis Based on the Julia Olefination Protocol

A new reagent for the synthesis of the α,β‐unsaturated N ‐methoxy‐ N ‐methyl‐amide structural unit has been developed. 2‐(Benzo[ d ]thiazol‐2‐ylsulfonyl)‐ N ‐methoxy‐ N ‐methylacetamide, a crystalline solid with an indefinite shelf life that can be easily prepared in two convenient steps from 2‐chloro‐ N ‐methoxy‐ N ‐methylacetamide, reacted with a variety of aldehydes under Julia conditions to furnish the α,β‐unsaturated N ‐methoxy‐ N ‐methyl‐amide functionality. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)