Английская Википедия:2-Acetylfuran

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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.[3] 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 Flavourant

Described to have a Balsamic, Caramellic, Sweet, Almond, Nutty profile with recommended uses in Bakery, Chocolate, Cocoa, Coffee, Nut, Tomato.[7]

See also

References

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