5-(4-Chlorophenyl)-2-furanmethyl methyl ketone is useful as an antifungal agent.

This invention is concerned with the compound 
5-(4-chlorophenyl)-2-furanmethyl methyl ketone. 
This compound possesses antifungal activity and is useful in the prevention 
of fungal growth. It is particularly inimical to Candida albicans in the 
commonly employed in vitro technique for determining antifungal activity 
at a concentration of 80 mcg of compound per milliliter of test media. It 
is also inimical to the growth of Microsporum canis at a level of 100 mcg 
per milliliter of test media in similar in vitro assays. 
This compound is readily combined with various adjuvants and excipients 
known to the art to provide antifungal compositions. 
In order that this invention may be readily available to and understood by 
those skilled in the art, the currently preferred method for preparing the 
compound thereof is described.

A. 2-(4-Chlorophenyl)-5-(2-nitro-1-propenyl)furan 
A mixture of 82 g (0.4 mole) of 5-(p-chlorophenyl)-2-furaldehyde in 400 ml 
of nitroethane together with 4 ml of piperidine was heated at reflux for 2 
hours. 
After overnight standing, crystalline solid separated. The mixture was 
filtered and the solid was washed well with hexane and air dried. The 
yield was 53 g (50%). 
Recrystallization of 26.5 g from 200 ml of ethyl acetate gave 19.5 g, m.p. 
136.degree.-139.degree.. 
Anal. Calcd. for C.sub.13 H.sub.10 Cl NO.sub.3 : C, 59.21; H, 3.82; N, 
5.31. Found: C, 58.91; H, 3.79; N, 5.25. 
B. 5-(4-Chlorophenyl)furfuryl Methyl Ketone 
A mixture of 167 g (0.63 m) of A. 320 g of iron powder, and 1 g. of ferric 
chloride in 1600 ml of glacial acetic acid was warmed on a steam bath with 
stirring. Vigorous reaction set in when the temperature reached about 
80.degree.. The reaction mixture became quite thick while the temperature 
went up to 120.degree.. After the initial reaction subsided (about 20 
min.), the mixture was allowed to stir for another 40 min. The mixture was 
further warmed on a steam bath with stirring for 1/2 hr. and then 150 ml 
of conc. HCl was added in about 15 min. After an additional warming with 
stirring for 13/4 hr. the reaction mixture was allowed to cool overnight. 
The reaction mixture was filtered and the brown solid was washed with 
glacial acetic acid. The filtrate was concentrated in a water bath at 
reduced pressure. The residual gummy material was triturated with water to 
give a solid. The mixture was filtered and the solid was further 
triturated with dilute HCl solution, filtered washed well with water and 
air-dried to give 130 g of crude product. 
Extraction of 120 g with hot hexane (4 l) and subsequent concentration of 
the hexane extract to about 1 l gave 77 g of orange crystalline solid on 
cooling. A second crop of 22 g was obtained by concentrating the filtrate. 
The combined yield was 99 g (67%). Recrystallization of 77 g from hexane 
gave 62 g, m.p. 54.degree.-56.degree.. 
Anal. Calc'd. for C.sub.13 H.sub.11 ClO.sub.4 : C, 66.53; H, 4.72. Found: 
C, 66.47; H, 4.74.