ORGLIST: On the reduction of thiochromene!

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From: 段智明 (rutheniumduan$##$hotmail.com)
Date: Thu Oct 26 2006 - 07:37:24 EDT

Hi everybody,
I'm a newcomer in this community.I have some troubles in the selective reduction of thiochromene recently.I want to reduce the carbonyl group to alcohol and keep the double bond intact.Firstly, by the way the solubility of the substrate is poor in common solvent,I've tried NaBH4/CeCl3 system,and the results seem to be unexpected.The precipitation was obtained and it seem to be a complex of the substrate and cerium ion. Secondly,I tried to carry out the reduction at reflux in methanol by just adding NaBH4,but the double bond reducing products were obtained. What can I do? Is there any reducing system suitable for thiochromene?
                                                    Zhiming Duan
                                               2006.10.26 from Beijing ICCAS
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