410097-82-4

Upstream product

• 288-32-4 1H-imidazole 
• 100-52-7 benzaldehyde 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 583-03-9 1-Phenyl-1-pentanol 
• 3835-64-1 2,2-dimethyl-1-phenylpropan-1-ol 
• 91-01-0 1,1-Diphenylmethanol 
• 98-85-1 1-Phenylethanol 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Tuning the reactivity of O-tert-butyldimethylsilylimidazolyl aminals towards organolithium reagents

O-tert-Butyldimethylsilylimidazolyl aminals are N,O-acetals that form readily from aldehydes, and although they function as aldehyde stabilizing and protecting groups under various conditions, we report here that they react with organolithium reagents similarly to the parent aldehydes. The mechanism involves the intermediate formation of a 2-imidazolyl anion as is exemplified by the isolation of 2-TBDMS-imidazole. Substitution of the imidazolyl moiety at the 2-position renders these aldehyde derivatives stable to organolithium reagents, thus allowing for the tuning of their reactivity.

A Convenient Protecting Group for Aldehydes

Aldehydes were cleanly and chemoselectively protected by treatment with tert-butylchlorodimethylsilane and imidazole. The resulting O-tert-butyldimethylsilylimidazolyl aminals were deblocked under mild conditions by employing 9:1. CH3CN - 49 percent HF.