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Usage

Uses

Used in Pharmaceutical Industry:
1-(2-(CHLOROMETHYL)-5-PHENYLFURAN-3-YL)ETHANONE is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique structure and reactivity allow for the creation of new molecules with potential therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical field, 1-(2-(CHLOROMETHYL)-5-PHENYLFURAN-3-YL)ETHANONE serves as a key intermediate in the synthesis of various agrochemical products. Its potential to be transformed into compounds with pesticidal or herbicidal properties makes it a valuable component in the development of crop protection solutions.
Used in Academic Research:
1-(2-(CHLOROMETHYL)-5-PHENYLFURAN-3-YL)ETHANONE is utilized as a research compound in academic settings. Its versatile chemical structure and reactivity make it an interesting subject for studies aimed at understanding organic reactions, exploring new synthetic routes, and discovering novel applications in various fields.

Upstream product

• 123-54-6 acetylacetone 
• 1074-12-0 phenylglyoxal hydrate 
• 89201-18-3 3-acetyl-1-phenyl-2-pentene-1,4-dione 

Downstream Products

• 528838-25-7 3-acetyl-2-hydroxymethyl-5-phenylfuran 

Relevant academic research and scientific papers

Acid-catalyzed convenient transformation of 1-aryl-2-pentene-1,4-diones into polyfunctionalized furans

The reaction of phenylglyoxal with 2,4-pentanedione in the presence of boron trifluoride gave the unstable 3-acetyl-1-phenyl-2-pentene-1,4-dione intermediate which was converted in situ by the reaction with an excess amount of 2,4-pentanedione into new crystalline tri- and tetra-substituted furans. Other unstable 1-aryl-2-pentene-1,4-diones, which were obtained by the photooxygenation of 3-acetyl-5-aryl-2-methylfurans, were trapped by the acid-catalyzed reaction, giving polyfunctionalized furans in good yields. Treatment of the 1-phenyl-2-pentene-1,4-dione intermediate with concentrated hydrochloric acid followed by boiling ethanol quantitatively yielded a stable 2-ethoxymethylfuran via the unstable 2-chloromethylfuran. (C) 2000 Elsevier Science Ltd.

Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1,4-diones

The BF3-catalyzed cyclization of 3-acetyl-1-aryl-2-pentene-1,4-diones 1a-e in the presence of water in boiling tetrahydrofuran gave bis(3-acetyl-5-aryl-2-furyl)methanes 2a-e in 26-79% yields along with a small amount of 3-acetyl-5-aryl-2-methylfurans 3a-e. The exact structure of 2a was determined by X-ray crystallography. The use of a half volume of the solvent for the reaction of 1a resulted in the formation of 2,4-bis(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-phenylfuran (4) together with 2a and 3a. A similar reaction of 1a was carried out in the presence of 3-acetyl-5-(4-methylphenyl)-2-methylfuran (3d) to afford 4-(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-(4-methylphenyl)-2-methylfuran (5) in 49% yield. The BF3-catalyzed reaction of 1a with 2,4-pentanedione in dry tetrahydrofuran at 23°C gave 3-(3-acetyl-5-phenyl-2-furfuryl)-4-hydroxy-3-penten-2-one (6a) and 3-(3-acetyl-2-methyl-4-phenyl-5-furyl)-4-hydroxy-3-penten-2-one (7a) in 66 and 24% yields, respectively. The product distribution depended on the reaction temperature. A similar reaction of 1b-e also yielded the corresponding trisubstituted furans 6b-e and tetrasubstituted furans 7b-e in good yields. These results suggested the presence of the furfuryl carbocation intermediate A during the reaction. The one-pot synthesis of 6a and 7a was also achieved by a similar reaction using phenylglyoxal. The deoxygenation of 1a with triphenylphosphine gave 3a in 88% yield, while 1a was treated with concentrated hydrochloric acid to yield 3-acetyl-2-chloromethyl-5-phenylfuran (8) which was quantitatively transformed in ethanol into 3-acetyl-2-ethoxymethyl-5-phenylfuran (9) and in water into 3-acetyl-5-phenylfurfuryl alcohol (10), respectively. In addition, the Diels-Alder reaction of cyclopantadiene with 1a gave the corresponding [4+2] cycloaddition products 11 and 12.