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.
Synthesis
2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl
Grignard reagent
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide ...
on
2-furonitrile
2-Furonitrile is a colorless derivative of furan possessing a nitrile group.
Synthesis
Industrial synthesis is based on the vapor phase ammoxidation of furfural with ammonia over bismuth molybdate catalyst at 440-480 °C.
Numerous labora ...
.
Modern industrial synthesis generally involves the
Friedel–Crafts acylation of
furan
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.
Furan is a colorless, flammable, highly ...
with
acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a col ...
.
Applications
Pharmaceuticals
A one-pot synthesis of an intermediate to the
HIV integrase
Retroviral integrase (IN) is an enzyme produced by a retrovirus (such as HIV) that integrates—forms covalent links between—its genetic information into that of the host cell it infects. Retroviral INs are not to be confused with phage inte ...
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.
[
]
See also
*
Isomaltol - same core, with a hydroxy group in the 3-position
*
2-Furoic acid
References
{{DEFAULTSORT:Acetylfuran, 2-
2-Furyl compounds