With sodium telluride in l-methyl-2-pyrrolidinone

Aromatic aldehydes are reduced to the corresponding alcohols by the title system.  

The regioselective reduction of the C=C bond of a, -unsaturated carbonyl compounds, a very important organic reaction, is achieved by means of hydrogen telluride and phenyl tellurol, under appropriate experimental conditions. 

When the phenyl tellurol is prepared by methanolysis of phenyltellurotrimethylsilane, both the C=C bond and the carbonyl group can be reduced.  

3-Phenylpropaml (typical procedure) NaHTeA stirred mixture of Te powder (0.65 g, 5 mmol) and NaBH4 (0.45 g, 11.8 mmol) in EtOH (20 mL) is heated under argon. After 15 min most of the Te had dissolved. The mixture is then cooled at -20°C and treated with a deoxygenated solution of HOAc (0.6 mL) in EtOH (2.5 mL). 

Reduction To the above-prepared solution of NaHTe is added 3-phenylpropenal (0.264 g, 2 mmol) in EtOH (2 mL). The mixture is stirred at room temperature for 4-5 h, then filtered from the formed black Te through Celite and the filtrate evaporated. The residue is purified by distillation, giving the pure product (0.265 g (99%)). 

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