151502-67-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 77924-28-8 4-tert-butyl 1-ethyl 2-(diethoxyphosphoryl)succinate 
• 157188-05-1 2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-succinic acid 4-tert-butyl ester 1-ethyl ester 

Downstream Products

• 538343-03-2 ethyl 4-hydroxy-6-methoxynaphthalene-2-carboxylate 
• 151502-73-7 ethyl 4-acetoxy-6-methoxynaphthalene-2-carboxylate 

Relevant academic research and scientific papers

An efficient method for the synthesis of substituted 4-acetoxynaphthalene- 2-carboxylate esters, ethyl 4-acetoxybenzofuran-6-carboxylate, and ethyl 4-acetoxybenzothiophene-6-carboxylate

4-Acetoxynaphthalene-2-carboxylate esters and their corresponding benzofuran and benzothiophene esters are important synthetic intermediates for the preparation of analogs of CC-1065 and the duocarmycins. In this communication, an efficient method for the synthesis of the titled compounds using an Emmons-Horner reaction strategy is reported. As an alternative to the Stobbe condensation reaction, coupling of tert-butyl 3-ethoxycarbonyl-3- (phosphonodiethyl)propionate with a series of aromatic aldehydes, followed by acid promoted removal of the tert-butyl group and Friedel-Crafts reaction, produced the target compounds in good overall yields and of excellent quality.

tert-Butyl-3-carboxyethyl-3-phosphonodiethylpropionate. A novel reagent for Stobbe-like condensations

tert-Butyl-3-carboxyethyl-3-phosphonodiethylpropionate was prepared and reacted with a range of aldehydes to give, after hydrolysis, itaconic half esters.