2-Acetylfuran Explained

2-Acetylfuran has a low melting point and a high boiling point.^{[1] [2]} The solid melts at 30 °C and has a density of 1.0975 g/ml at 20 °C, while the normal boiling point of the liquid is 168 - 169 °C.^[3] 2-Acetylfuran is a useful intermediate in the synthesis of fine chemicals and pharmaceuticals, and is used in the production of the generic cephalophosphorin antibiotic cefuroxime.^[4]

Synthesis

2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl Grignard reagent on 2-furonitrile.Modern industrial synthesis generally involves the Friedel–Crafts acylation of furan with acetic anhydride.

Applications

Pharmaceuticals

A one-pot synthesis of an intermediate to the HIV integrase inhibitor S-1360 was based on the Friedel-Crafts alkylation of 2-acetylfuran with 4-fluorobenzyl chloride using zinc chloride catalyst.^[5]

Reaction of 2-acetylfuran with aqueous sodium nitrite gave 2-furanyloxoacetic acid, an intermediate to Cefuroxime, a second-generation cephalosporin antibiotic.^[6]

Artificial flavouring

This compound has a balsamic, caramellic, sweet, almond, nutty profile with recommended uses in bakery, chocolate, cocoa, coffee, nut and tomato products.^[7]

See also

• Isomaltol - same core, with a hydroxy group in the 3-position
• 2-Furoic acid

Notes and References

1. Howard D. Hartough. Acylation of thiophene and furan by means of boron trifluoride. VII. Journal of the American Chemical Society. 70 . 867. 1948. Kosak. Alvin I.. 2. 10.1021/ja01182a510 .
2. Walther Borsche. Cleavage of the furan ring by primary aromatic amines and hydrochloric acid. Berichte der Deutschen Chemischen Gesellschaft B. 71. 957–66. 1938. Leditschke. Heinrich. Lange. Karl.
3. Y. . Asahina. Ethereal oil of Elsholtzia cristata Willdenow (Lablatae). Archiv der Pharmazie. 252. 435–48. 1914 . Murayama. Y.. 10.1002/ardp.19142520609. 94708979.
4. Rong-geng Wang. Side chain of cefuroxime: (Z)-2-methoxyimino-2-(fury-2-yl)acetic acid ammonium salt. Jingxi Yu Zhuanyong Huaxuepin. 12 . 17. 10–11. 2004. Liu. Cheng-ping. Zhu. Kun-peng. Du. Hai-lin . Liu. Lie-yi .
5. Kenji Izumi. One-Step Synthesis of 5-(4-Fluorobenzyl)-2-furyl Methyl Ketone: A Key Intermediate of HIV-Integrase Inhibitor S-1360. Organic Process Research & Development. 11 . 6. 1059–1061. 2007. Kabaki. Mikio. Uenaka. Masaaki. Shimizu. Sumio. 10.1021/op700117q.
6. Rui-min Lv. The research for the synthesis of 2-methoxyimino-2-furylacetic acid. Shandong Huagong. 34 . 6. 5–8. 2005. Zhang. Zhi-de. Zhang. Zhi-cheng.
7. Web site: Online Compendium .