541-57-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2(5H)-furanone is used as a reagent for the preparation of hydroxylated piperidine alkaloids, which are important in the synthesis of various pharmaceutical compounds. Its ability to react with other molecules makes it a valuable component in the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Hydroxy-2(5H)-furanone is used as a building block for the creation of various organic compounds. Its furanone structure allows for further functionalization and modification, making it a useful starting material for the synthesis of complex molecules.
Used in Research and Development:
Due to its unique chemical properties, 4-Hydroxy-2(5H)-furanone is also utilized in research and development for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C4H4O3/c5-3-1-4(6)7-2-3/h1,5H,2H2

Upstream product

• 21151-51-9 3-bromo-4-hydroxyfuran-2(5H)-one 
• 35594-15-1 ethyl 4-acetoxyacetoacetate 
• 128766-63-2 6-hydroxymethyl-2,2-dimethyl-4H-1,3-dioxin-4-one 
• 15667-21-7 D-erythronolactone 
• 623-86-9 acetoxy-acetic acid ethyl ester 
• 69556-70-3 4-methoxy-5H-furan-2-one 

Downstream Products

• 109480-19-5 4-Hydroxy-3-phenylacetyl-5H-furan-2-one 
• 115580-38-6 3,3-dicinnamyldihydrofuran-2,4-dione 
• 106536-22-5 3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione 
• 115580-39-7 3-(2-cyclohexen-1-yl)-4-hydroxy-5H-furan-2-one 
• 115580-40-0 3,3-di-(2-cyclohexen-1-yl)-3H,5H-furan-2,4-dione 
• 114646-13-8 3-nitrotetronic acid 
• 94512-55-7 4-Hydroxy-3-(4-nitro-phenylazo)-5H-furan-2-one 
• 69556-75-8 4-(benzyloxy)-2(5H)-furanone 
• 114908-93-9 3-(1,1-dimethyleth-1-yl)-4-hydroxy-2(5H)-furanone 
• 30290-18-7 4-(methylamino)furan-2(5H)-one 
• 155140-39-9 4-iodo,2(5H)-furanone 
• 486403-43-4 4-(2-amino-4-methylanilino)-2,5-dihydro-2-furanone 
• 638202-95-6 4-(2-vinylcyclopentanyloxy)furan-2(5H)-one 
• 471931-08-5 4-(p-toluenesulfonyloxy)-2(5H)-furanone 

Relevant academic research and scientific papers

Novel synthesis technology of tetronic acid

The invention provides a novel synthesis technology of tetronic acid. According to the technology, cheap glycollic acid ester easy to obtain is adopted as an initial precursor and reacts with acetyl halides, a key intermediate 2-acetoxyl acetate is obtained, then, dickman condensation is perfomed on the alkaline condition, and the target product tetronic acid is obtained. The raw materials are easy to obtain, reaction conditions are mild, operation is easy and convenient, the synthesis cost is low, and large-scale industrial production is convenient. The final product tetronic acid is high in purity and yield, and the yield can reach 93% or above.

A method for synthesizing tetranoic acid

The invention discloses a synthetic method of tetronic acid. The synthetic method comprises the following steps: firstly oxidizing low-price easily-available natural sodium D-isoascorbate as a raw material through hydrogen peroxide, and acidifying through hydrochloric acid to prepare a key synthetic intermediate, namely erythronolactone; secondly, reacting erythronolactone with sulfonyl chloride to generate crude tetronic acid; finally, simply re-crystallizing obtained crude tetronic acid to obtain pure tetronic acid. The synthetic method has the characteristics of few synthetic steps, simple and convenient process, low synthetic cost, convenience for large-scale industrialized production and the like; finally obtained pure tetronic acid is high in yield and purity, the yield can reach more than 87%, and the purity can reach more than 99%.

Unexpected facile synthesis of tetronic acid during the research on stereospecific total synthesis of (+)-biotin starting from D-erythorbic acid as chiral pool

The reaction of D-erythronolactone (8) with the methanesulfonyl chloride in the presence of triethylamine afforded, after unexpected elimination reaction, the tetronic acid is obtained in excellent yield and chemical purity, instead of the dimesylates (7)

Process for the Preparation of Tetronic Acid

Tetronic acid of following Formula (2): is industrially efficiently prepared through a reaction of 4-hydroxy- or 4-alkoxy-acetoacetic acid or an ester thereof of following Formula (1): wherein R1 and R2 each independently represent a hydrogen atom or an alkyl group, by carrying out the reaction in the presence of an organic solvent and an acid but substantially in the absence of water. Product tetronic acid is useful as an intermediate for fine chemicals such as pharmaceuticals, agricultural chemicals, and semiconductor resist polymers.

Substitution and Michael Reactions of Bicyclic Tetronic, Tetramic and Thiotetronic Esters

The 1,4-addition of several heteroatom and carbon nucleophiles to the bicyclic structures 1, 2, 3, and 13 are reported along with the conversion of the resultant adducts to substituted tetronic, tetramic, thiotetronic acids and butenolides; a novel reaction mechanism has been observed for the iodotrimethylsilane (TMSI) or acetic anhydride/magnesium bromide-mediated furan ring-opening reactions of the bicyclic tetronate 1.

A LABORATORY SYNTHESIS OF 4-HYDROXY-2-(5H)-FURANONE (β-TETRONIC ACID)

A "one pot"-fashioned preparation of 4-hydroxy-2(5H)-furanone (β-tetronic acid) was conducted in 30-40percent overall yield starting from ethyl acetoacetate.