P. Malik, D. Chakraborty / Tetrahedron Letters 51 (2010) 3521–3523
3523
References and notes
4
-OMeC H COOH
6 4
0
0
0
0
0
.4
.3
.2
.1
.0
4
-OMeC H CHO
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6
with 10 mol % Bi
conditions.
2 3
O and 5 equiv 70% t-BuOOH (water) in EtOAc under reflux
7.
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(
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3
. Conclusions
In summary, we have developed a simple, efficient, chemoselec-
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1
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1
4
2
O
3
.
It is noteworthy to mention that this method does not
8
.
.
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9
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1
1
0. Encyclopedia of Reagents for Organic Synthesis, Vol. 1, p 538.
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Acknowledgements
This work was supported by Department of Science and
Technology and Council of Scientific and Industrial Research,
New Delhi. The services from the NMR facility purchased under
the FIST program, sponsored by the Department of Science and
Technology, New Delhi, are gratefully acknowledged.
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2
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14. Typical experimental procedure: To
0.10 mmol) and aldehyde (1 mmol) in 2.5 mL EtOAc was added 70% t-BuOOH
water) (0.90 mL, 5 mmol). The reaction mixture was heated to reflux. The
progress of the reaction was monitored using TLC until all aldehyde was found
consumed. The crude product was treated with saturated NaHCO solution.
a
2 3
stirred suspension of Bi O (68 mg,
(
3
Supplementary data
This was extracted with ethyl acetate. Finally, the aqueous layer was acidified
using 2 N HCl and extracted with ethyl acetate. The organic layer was
concentrated and subjected to column chromatography. The spectral data of
the various carboxylic acids were found to be satisfactory in accordance with
the literature (see Supplementary data for details).