Base-Mediated Tandem Reaction Consisting of an Acyl Shift Strategy
Csp2 bond, in one step. Work to extend this transfor-
mation in organic synthesis is currently underway.
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Experimental Section
Typical Experimental Procedure for Base-Mediated
Tandem Reaction Consisting of an Acyl Shift
Strategy
A mixture of substrate 1 (0.3 mmol), anhydrous KOAc
(4 equiv.), 4ꢁ molecular sieve (100 mg) and anhydrous
MeCN (2 mL) was stirred in a Schlenk tube at 1008C (oil
bath temperature) under an argon atmosphere until com-
plete consumption of starting material as monitored by TLC
and GC-MS analysis. Then the mixture was filtered through
a column, washed with diethyl ether, and evaporated under
vacuum. The residue was purified by flash column chroma-
tography (hexane/ethyl acetate) to afford the pure product
2.
4,5-Diphenylfuran-2(5H)-one (2a):[12] Yellow solid, mp
1
149–1518C (uncorrected); H NMR (500 MHz, CDCl3): d=
7.38–7.42 (m, 2H), 7.31–7.36 (m, 8H), 6.55 (d, J=1.5 Hz,
1H), 6.33 (d, J=1.5 Hz, 1H); 13C NMR (125 MHz, CDCl3):
d=172.6, 165.8, 134.9, 131.3, 129.7 (2C), 129.2, 129.0, 127.9,
127.6, 114.7, 84.4; IR (KBr): n=1748 cmÀ1; LR-MS (EI,
70 eV): m/z (%)=236 (M+, 44), 207 (15), 131 (34), 102
(100), 77 (19).
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Acknowledgements
We thank the Scientific Research Fund of Hunan Provincial
Education Department (Nos. 08C582 and 08A037), and Na-
tional Natural Science Foundation of China (No. 20872112)
for financial support.
ˇ
e) M. Pour, M. Spulꢃk, V. Buchta, P. Kubanovꢃ, M.
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