6141-57-7

Usage

Uses

Used in Organic Synthesis:
METHYL 3-METHYL-2-FUROATE is used as a key intermediate in the synthesis of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Pharmaceutical Industry:
METHYL 3-METHYL-2-FUROATE is used as a building block in the production of pharmaceuticals, aiding in the development of new drugs and improving the efficacy of existing medications.
Used in Agrochemical Industry:
METHYL 3-METHYL-2-FUROATE is used as a raw material in the synthesis of agrochemicals, such as pesticides and herbicides, helping to increase crop yields and protect plants from pests.
Used in Dye Industry:
METHYL 3-METHYL-2-FUROATE is used as a precursor in the production of dyes, contributing to the creation of new colorants and enhancing the performance of existing dyes in various applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 21, p. 102, 1956 DOI: 10.1021/jo01107a021

InChI:InChI=1/C7H8O3/c1-5-3-4-10-6(5)7(8)9-2/h3-4H,1-2H3

Upstream product

• 67-56-1 methanol 
• 22601-06-5 3-methylfuran-2-carbonyl chloride 
• 99183-76-3 methyl 5,5-dimethoxy-3-methyl-2,3-epoxypentanoate 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 96-34-4 methyl chloroacetate 
• 186581-53-3 diazomethane 
• 4412-96-8 3-methylfuran-2-carboxylic acid 
• 33342-48-2 3-methyl-2-furfuraldehyde 
• 930-27-8 3-methylfuran 

Downstream Products

• 20416-16-4 (3-methylfuran-2-yl)methanol 
• 2528-01-0 5-bromo-3-methylfuran-2-carboxylic acid methyl ester 
• 441016-68-8 methyl 4,5-dibromo-3-methyl-2-furancarboxylate 
• 845652-41-7 C₁₃H₁₀Cl₂O₃ 
• 934340-46-2 C₁₄H₁₃ClO₄ 
• 934340-44-0 C₁₃H₁₁ClO₃ 
• 22601-06-5 3-methylfuran-2-carbonyl chloride 
• 1127217-59-7 methyl 3-methyl-5-(o-tolyl)furan-2-carboxylate 

Relevant academic research and scientific papers

Synthetic studies on pseudolaric acid B: Enantioselective synthesis of C4,C10-di-epi-trans-fused [5-7]-bicyclic skeleton

Studies on the synthesis of antifungal and anticancer natural product, pseudolaric acid B, have led to the enantioselective synthesis of di-epi-trans-fused [5–7]-bicyclic core skeleton. The synthesis was achieved in 10 linear steps, which features the Sharpless asymmetric epoxidation, cyanide-opening reaction of epoxide, and intramolecular [5 + 2] cycloaddition reaction as the key transformations. The stereochemistry was determined by the X-ray crystallographic analysis.

Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions

By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (?)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(?)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furanmethanol take place in both the ground and excited states. The results of computational studies show that geometries of C2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.

3-Substituted-(5-arylfuran-2-ylcarbonyl)guanidines as NHE-1 inhibitors

The C-3 substituents effect on NHE-1 inhibitory activity of (5-arylfuran-2-ylcarbonyl)guanidines, previously identified as potent NHE-1 inhibitors, was investigated. The introduction of amine or alkyl groups at the 3-position of the furan ring, next to the acylguanidine moiety, remarkably improves NHE-1 inhibitory potency. Especially the important finding is that 5-(2,5-dichloro)phenyl and 5-(2-methoxy-5-chloro)phenyl derivatives exhibit high NHE-1 inhibitory activities (IC50 0.02 μM) that match those of 3-unsubstituted derivatives.

Anionic [4+2] cycloaddition strategy to linear furocoumarins: Synthesis of 8 methoxypsoralen and its isoster

The surfoxide esters 14 and 20d are successfully annulated with bicyclic enone 8 in the presence of (t)BuOLi to provide the pentacyclic ketones 9a and 21a respectively in good yields (≤70%). Flash vacuum pyrolysis of O-methyl derivatives 9b and 21b at - 5000 C/. 1 mm provide furoindacenones 16b and 22b respectively, which in turn are convertible to furocoumarins 1 and 3.

VOLATILE CONSTITUENTS OF CLAUSENA WILLDENOVII: STRUCTURES OF THE FURANOTERPENES α-CLAUSENAN, DICLAUSENAN A AND DICLAUSENAN B

Four furanoid terpenic compounds, α-clausenan, rosefuran (γ-clausenan) and diclausenans A and B, were isolated from the essential oil of the leaves of Clausena willdenovii.Their structures were determined by chemical and spectral data.The occurence of a high concentration of rosefuran is noteworthy.Selenium dioxide oxidation of diclausenan gave an unusual product, identified as an epoxy-dicarbonyl compound. - Keywords: Clausena willdenovii; Rutaceae; furanoterpenes; α-clausenan; γ-clausenan (rosefuran); diclausenans A and B.