Methyl 3-phenylpropionate → Benzenepropanol

Participants

Reaction Steps

A 30-mL eggplant flask equipped with a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with nitrogen atmosphere. To the flask, methyl 3-phenylpropionate (167 mg, 1.0 mmol) and 1,1,3,3-tetramethyldisiloxane (336 mg, 2.5 mmol) were added through a syringe, and iron complex A (15 mg, 0.03 mol) was added as catalyst. The solution was stirred at room temperature for 3 hours. At 0° C., THF (1 mL) and tetrabutylammonium fluoride in THF (1 M, 1 mL) were then added to the solution, which was stirred at 0° C. for 1 hour. THF was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (5/1) as developing solvent, obtaining 3-phenylpropan-1-ol (131 mg, 0.96 mmol, 96%). The results are shown as Entry 1 in Table 8. The resulting alcohol was identified for geometry by 1H and 13C-NMR spectroscopy.

Provenance & Evidence