Methyl 3-phenylpropionate → Benzenepropanol

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.

1. customA 30-mL eggplant flask equipped with a magnetic stirrer
2. temperaturewas heat
3. customdried
4. customwas purged with nitrogen atmosphere
5. additioniron complex A (15 mg, 0.03 mol) was added as catalyst
6. stirringwas stirred at 0° C. for 1 hour
7. distillationTHF was distilled off in vacuum
8. customThe crude product was purified by silica gel-

ORD record

ord-064261e574c942898124d79c523aa98e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09421532B2