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2 Acetylfuran

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Appearance  Low melting solid
2-Acetylfuran httpsuploadwikimediaorgwikipediacommonsthu

2-Acetylfuran is a low melting solid or high boiling liquid, depending on temperature. 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. 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.

Contents

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.

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.

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

References

2-Acetylfuran Wikipedia


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