Sulfone, methyl methylthiomethyl alkylation

Synthesis of Esters and Aldehydes. Monoalkylation of methylthiomethyl p-tolyl sulfone (MT-sulfone) with an alkyl halide is achieved by the action of a phase-transfer catalyst (PTC) in toluene-50% aq NaOH. sodium hydride and butyl-lithium also generate a carbanion of MT-sulfone. Arylmethyl derivatives of MT-sulfone are prepared by sodium borohydride reduction of the Knoevenagel condensation products with aromatic aldehydes. The monoalkylated products are converted into the corresponding methyl esters (eq 1). This functionalization can be utilized for synthesizing a-alkoxy carboxylic esters (eq 2) and Q -amino acids (eq 3). ... 

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