
TY  - JOUR
A1  - Elix, JA 
A1  - Ferguson, BA 
T1  - Annelated furans. XIII. Methylation of 3-Acylbenzofuran-2(3H)-ones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 5
SP  - 1079
EP  - 1091
KW  - 
UR  - https://doi.org/10.1071/CH9731079 
N2  - Methylation of 3-acylbenzofuran-2(3H)-ones with diazomethane generally led to a mixture of 3-acyl-2-methoxybenzofuran and 3-(&#945;- methoxy)alkylidenebenzofuran-2(3H)-one. These reactions provided the first evidence for the existence of 3-acylbenzo- furan-2(3H)-ones in the 3-acyl-2-hydroxybenzofuran tautomeric form as well as the widely accepted 3-(or-hydroxy)alkylidenebenzofuran-2(3H)one form. In general, methylation of the title compounds with methanol and sulphuric acid gave initially the corresponding 3-(&#945;-methoxy)alkylidenebenzofuran- 2(3H)one while prolonged reaction led to the formation of methyl 2- alkylbenzofuran-3-carboxylates. The mechanism of this acid-catalysed rearrangement and the rearrangement of 3-acetyl-2-methoxybenzo- furan were studied.     The reaction of 3-acetylbenzofuran-2(3H)-one with methyl iodide and potassium carbonate gave a mixture of 3,3-dimethylbenzo-furan-2(3H)-one and 3-methylbenzofuran-2(3H)-one. These products were also obtained by methylating benzofuran-2(3H)-one under similar conditions. 
ER  -

