Chemistry Letters 2000
845
There have been some reports where the primary hydroxyl
group of 1,2-diols is oxidized in presence of secondry alcohols.
9
C. Betancor, C. G. Francixco, R. Freire, and E. Suarez, J.
Chem. Soc., Chem. Commun., 1988, 947.
24
The oxidation of 1,2-diols appears to be a straightforward route
to prepare α-hydroxy aldehydes. However the present method
provides α-hydroxy ketones without formation of α-hydroxy
aldehydes.
10 a) S. K. Kang, K. Y. Jung, C. H. Park, E. Y. Namkoong, and
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The typical procedure involves stirring a mixture of the
ammonium molybdate (1 mmol) and epoxide (1 mmol) in THF.
Hydrogen peroxide (2 mL of 30% aquoeus solution) was added
and the reaction proceeded at room temperature. After comple-
tion of reaction as indicated by tlc, the reaction mixture was fil-
tered off and washed with water, extracted with chloroform. The
organic layer was separated and dried over Na SO . The residue
11 J. J. Bloomfield, D. C. Owsley, C. Ainsworth, and R. E.
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2
4
was purified by silica gel using hexane : ethyl acetate (7 : 3) as
eluent to get pure product in good yield. All the products have
13 T. L. Ho and G. A. Olah, Synthesis, 1976, 815.
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1
been characterized by H NMR, IR, mass spectroscopy.
In conclusion, a synthetically useful and practical approach
for the preparation of α-hydroxy ketones in one-pot by the
opening of epoxides with ammonium molybdate–H O system
2
2
has been developed. This method has a potential for the prepa-
ration of α-hydroxy ketones of biological interest.
The authors wish to thank Dr. K. V. Raghavan, Director
IICT for kind permission to communicate the results and Mr.
M. Arifuddin, SRF, Organic Chemistry Division I, IICT for his
constant help and discussion during the course of this work.
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2