One-Pot Two-Step Approach to Selenides. Phase-Transfer Catalyzed Synthesis of ω-Hydroxyalkyl Selenides

References

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• A general procedure for the preparation of ω-hydroxyalkyl selenides: To the mixture of selenium (4.0g, 50mmol) and sodium hydroxide (2.0g, 100mmol) in water (30ml), 85% hydrazine hydrate (1.0ml, 17mmol) was added dropwise under nitrogen. Stirring and heating it for about 3hr until all the selenium was consumed. Then 0.3g TBAB and ω-haloalkyl alcohol (50mmol) in ethyl ether (20ml) were added and refluxed. When the aqueous layer was nearly clear KBH4 (90mmol) and NaOH (60mmol) was added and refluxed until the solution became colorless, followed by dropping a solution of alkyl halide (75mmol) in ether (20ml). After refluxing 8hr, the mixture was allowed to cool down to room temperature. The ether layer was separated and the aqueous layer was extracted with ether for several times. The organic layers were combined and washed with water followed by brine and dried over anhydrous magnesium sulfate. After removing the solvent off the residue was purified by column chromatography on silica gel to afford pure product
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• Rongalite can also be used in the preparation and it is cheaper, but it easily deteriorates.
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