42588-57-8

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Ethoxymethacrolein is used as a key intermediate for the synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), which is an important compound in the development of pharmaceuticals targeting various health conditions.
Used in Organic Chemistry:
In the field of organic chemistry, 3-Ethoxymethacrolein is utilized as a starting material for the modified Friedlander synthesis, which is a method for the preparation of quinolines. Quinolines are a class of compounds with diverse applications, including their use as antimalarial, anticancer, and antituberculous agents.
Used in Fragrance Industry:
3-Ethoxymethacrolein is also used as a building block for the creation of 3-[2-isopropyl-5-methylcyclohexyloxy-(1R, 2S, 5R)]-2-methyl-2E-propenal, a compound that contributes to the development of unique fragrances and scents in the perfumery and fragrance industry.
These applications highlight the multifaceted nature of 3-Ethoxymethacrolein, showcasing its importance in various industries, from pharmaceuticals to organic chemistry and the fragrance sector.

InChI:InChI=1/C6H10O2/c1-3-8-5-6(2)4-7/h4-5H,3H2,1-2H3/b6-5+

Upstream product

• 10602-37-6 1,1,3,3-tetraethoxy-2-methyl-propane 
• 74-96-4 ethyl bromide 
• 107-31-3 Methyl formate 
• 123-38-6 propionaldehyde 
• 64-17-5 ethanol 
• 14477-99-7 1-bromo-2,2-dichloro-1-methylcyclopropane 
• 130894-82-5 1,2,2-trichloro-1-methylcyclopropane 
• 4744-08-5 1,1-diethoxypropane 
• 68-12-2 N,N-dimethyl-formamide 
• 14112-68-6 1-chloro-3,3-diethoxy-2-methyl-propene 

Downstream Products

• 71224-82-3 5-(2-Formylpropenylamino)-3-methylisoxazol 
• 71224-83-4 2-methyl-3-(3-phenyl-isoxazol-5-ylamino)-propenal 
• 71224-75-4 5-methyl-3-phenyl-isoxazolo[5,4-b]pyridine 
• 55424-75-4 7,16-dimethyl-5,14-dihydrodibenzo<1,4,8,11>tetraazacyclotetradecene 
• 111873-13-3 N,N'-di-(β-formyl-β-methylvinyl)-o-phenylene diamine 
• 111873-12-2 β-(o-aminophenylamino)-α-methyl-acrolein 
• 30567-26-1 (E)-2-methyl-hept-2-enal 
• 612-58-8 3-methylquinoline 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 87373-59-9 3-Cyano-5-methyl-2(1H)-pyridinethione 
• 49576-57-0 (2E)-2-methyloct-2-enal 
• 142114-71-4 5-methyl-2-(4-nitrophenyl)pyrimidine 1-oxide 
• 142114-72-5 2-(4-methoxyphenyl)-5-methylpyrimidine 1-oxide 
• 137595-48-3 3-Methyl-5-methoxyquinoline 

Relevant academic research and scientific papers

A facile route to 3-alkoxy-2-methylpropenals, useful intermediates in the synthesis of carotenoids

A 'one-pot' process for the preparation of a carotenoid synthon (4) has been developed that involves methoxide-promoted condensation of propionaldehyde with methyl formate, followed by exclusive O-alkylation of the resultant stabilized enolate (6).

Formation of acetylenic acetals by ring opening of 1,1,2-trihalocyclopropanes under phase-transfer conditions

A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonabk to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol. triethylbenzylammonium chloride and dichloromethane. most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford α,β-unsaturated aldehydes. Acta Chemica Scandinavica 1996.

Oxopropenylation of Alkylmagnesium Halides by 3-(Trimethylsilyloxy)acroleins

Oxopropenylation of alkylmagnesium halides 4 by 3-(trimethylsilyloxy)acroleins 3 selectively yields the (E)-isomers of α,β-unsaturated aldehydes such as 4-phenyl-2-butenals 9, 3-cyclopropylpropenals 10, 3-cyclohexylpropenals 11, 3-(3-menthyl)propenals 12, and 2,5-hexadienals 13. 3-Hydroxyenolsilylethers 6 are isolated when allylmagnesium chloride is used as carbon nucleophile; to conclude, the reaction primarily involves nucleophilic addition of the Grignard reagent at the aldehyde carbon of the acrolein 3.