2-Lithio-4-methylthiazole

Florio et al. have found that 2-lithio-4-methylthiazole can be conveniently generated almost quantitatively by the deprotonation of 4-methyl-thiazole with lithium diisopropylamide (LDA) in THF at -78 °C. Addition of a-chloroacetone to the solution yields the corresponding chlorohydrins. ... 

In an extensive temperature study on the lithiation of 2-methylthiazole (157) J. Crousier reported (441) that three lithio salts are formed independently, and not through proton-metal equilibration, at low temperature (—78 C, as shown in Scheme 77). The 4-lithio derivative (160) is... 

A similar observation was made more recently in the case of 4-substituted 2-methylthiazoles by A. I. Meyers (442-444), who could identify the product resulting from a temperature increase from -78°C to room temperature of the lithio salt of 2,4-dimethylthiazole (161). 

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