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A novel and practical synthetic method of 3(2 H )‐furanone derivatives
Author(s) -
Sakai Takashi,
Yamawaki Akitoshi,
Ito Hiroshi,
Utaka Masanori,
Takeda Akira
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230447
Subject(s) - chemistry , potassium hydroxide , sodium hydroxide , furfural , halogenation , ethanol , alkaline hydrolysis , hydrolysis , organic chemistry , claisen condensation , condensation , medicinal chemistry , catalysis , physics , thermodynamics
A novel, convenient synthetic method of 5‐atyl‐2,2‐dimethyl‐3(2 H )‐furanones (aryl = C 6 H 5 , 2‐CH 3 C 6 H 4 , 3‐CH 3 C 6 H 4 , 4‐CH 3 C 6 H 4 , 2‐CIC 6 H 4 , 4‐CIC 6 H 4 , 2,4‐Cl 2 C 6 H 3 ) is described. It involves the Claisen‐Schmidt condensation (potassium hydroxide/ethanol) of aromatic aldehydes with 3‐hydroxy‐3‐methyl‐2‐butanone to give enones, whose bromination followed by alkaline hydrolysis (sodium hydroxide/ethanol) affords 3(2 H )‐furanone derivatives in 54–64% overall yields. The procedure is also applicable to nicotinaldehyde and furfural, although the yields are not satisfactory.