19957-75-6

Usage

Uses

Used in Perfume and Food Industries:
2(5H)-Furanone, 5-methoxy-4-methylis used as a fragrance ingredient for its pleasant, fruity odor, enhancing the aroma of perfumes and food products.
Used in Medicinal and Pharmaceutical Research:
2(5H)-Furanone, 5-methoxy-4-methylis used as a subject of interest in medicinal and pharmaceutical research due to its potential antimicrobial and antioxidant properties, which can contribute to the development of new treatments and therapies.

Upstream product

• 157904-76-2 3,4-diaza-6-methoxy-1-oxa-2-oxo-bicyclo<3.3.0>octene 
• 108858-40-8 (3aS,4S,6aR)-4-Methoxy-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 
• 108858-40-8 (3aS,4R,6aR)-4-Methoxy-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 

Relevant academic research and scientific papers

Preparation of 5-hydroxy-4-methyl-2(5H)-furanone

5-Hydroxy-4-methyl-2(5H)-furanone is prepared by cyclization of alkyl β-formylcrotonates by heating with dilute aqueous hydrochloric acid or, advantageously, in the presence of dilute aqueous hydrochloric acid and catalytic amounts of methanol as solubilizer, subsequent workup of the reaction mixture by distillation and, where appropriate, isomerization of the 5-methoxy- or 5-ethoxy-4-methyl-2(5H)-furanone, which is formed as byproduct, by heating with dilute hydrochloric acid.

PSEUDOESTERES Y DERIVADOS XXXIII. SINTESIS DE COMPUESTOS CICLOPROPANICOS POR FOTOLISIS DE PIRAZOLINAS OBTENIDAS POR CICLOADICION 1,3-DIPOLAR A LA 5-METOXI-2(5H)-FURANONA

By cycloaddition of 2-diazopropane to 5-methoxy-2(5H)-furanone (1) two regioisomeric 1-pyrazolines 3 and 4 are stereospecifically obtained.Both isomers give by photolysis, as major or sole compound, the same cyclopropane derivative 7.Hydrolysis of the bicyclic compound 7, followed by esterification, leads to cis open chain derivatives, which are appropiately functionalized for the synthesis of pyrethroids. a similar set of reactions, using diazomethane-d2 as dipolarophile, affords selectively deuterated cyclopropane derivatives.Palabras clave: Cicloadicion 1,3-dipolar, pirazolinas, fotolisis, ciclopropanos, piretroides.

Asymmetric 1,3-dipolar cycloadditions to 5-(R)-menthyloxy-2(5H)-furanone

Various diazo compounds, nitrile oxides, nitrones and azomethine ylides were examined in 1,3-dipolar cycloadditions to enantiomerically pure 5-(R)-menthyloxy-2(5H)-furanone 1a. Pyrazoline 9 was obtained in 100% c.y. as a mixture of 2 diastereoisomers in ratios up to 72:28, whereas pyrazoline 16 was obtained in 100% c.y. as a single enantiomer. Photochemically pyrazolines 9 and 10 have been converted to cyclopropanes 11 and 13. Under thermal conditions pyrazoline 9 is converted to 4-methyl-5-menthyloxy-2(5H)-furanone. Isoxazoles 21a-24a were obtained enantiomerically pure via nitrile oxide addition to 1a in 64-67% yield. Nitrone addition afforded isoxazolidines 27, 28 and 34 with complete anti-facial- and regiochemistry, but with endo-exo-selectivities up to 76%. Enantiomerically pure isoxazolidines were obtained in 25-75% yield. Pyrrolidine 36 was obtained diastereomerically pure in 81% c.y. Pyrrolidines 42 and 45, however, were obtained as diastereomeric mixtures in 37% resp. 6% yield.