4602-94-2

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 108-95-2 phenol 

Downstream Products

• 109277-91-0 (E)-2-(1-Hydroxy-propyl)-3-phenoxy-but-2-enedioic acid dimethyl ester 

Relevant academic research and scientific papers

A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water

The stereoselective formation of C-O, C-S and C-N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic sol

An efficient and green approach for the synthesis of vinyl aryl ethers in the presence of guanidine hydrochloride

A stereoselective procedure for vinyl aryl ether bond formation by direct coupling of dialkyl acetylenedicarboxylates and substituted phenols or naphthols under mild reaction conditions has been developed. Using guanidine hydrochloride as a new catalyst a

Diastereoselective O-vinylation of phenols using DMAD under mild reaction conditions

An efficient and straightforward pyridine-catalyzed method allowing selective O-vinylation of phenols with DMAD is reported. The reaction is diastereoselective and leads exclusively to (Z)-configuration in high yields. Copyright Taylor & Francis Group, LL

Trimethylamine catalyzed stereoselective reaction between dimethyl acetylenedicarboxylate and phenols

Stereoselective reaction of various substituted phenols with dimethyl acetylenedicarboxylate in the presence of a catalytic amount of aqueous trimethylamine solution in dichloromethane leads to dimethyl 2-phenoxymaleates in good to excellent yields under mild condition.

DABCO-catalyzed reaction of phenols or 1,2-diphenols with activated alkynes leading to the formation of alkenoic acid esters or 1,3-dioxole derivatives

The reaction of phenols or 1,2-diphenols with activated alkynes took place smoothly and rapidly in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) at room temperature and resulted in the formation of various alkenoic acid ester

A Selective and Versatile Synthesis of Substituted Chromones via Addition of Phenols to Dimethyl Acetylenedicarboxylate

Despite many published syntheses of chromones, none has been reported to be both selective for chromones and tolerant of ring substitution.The addition of substituted phenols to dimethyl acetylenedicarboxylate is now reported as a versatile high yield initial step in a simple three-step synthesis of chromone 2-carboxylic acids.Triethylamine being used to deprotonate the substituted phenol, the addition to dimethyl acetylenedicarboxylate proceeds under mild conditions and tolerates a wide range of functional groups on the phenol.Although not stereoselective, both fumarate and maleate aryloxy products of this addition can then be cyclized, according to a known method, to chromones without contamination by isomeric coumarins.Thus the addition reaction is a valuable component of a versatile and selective synthesis of substituted chromones.

Stereoselective Addition of Phenols to Dimethyl Acetylenedicarboxylate adsorbed on Alumina

Although phenols react with dimethyl acetylenedicarboxylate (DMAD) to give a mixture of both cis- and trans-addition products, the reaction with DMAD adsorbed on alumina gives cis-addition products stereoselectively.