Hydrochloric Acid → Methyl 2-oxo-3-phenylpropanoate

Temperature

0 °C

2-Oxo-3-phenylpropanoic acid (20 g), DMF (100 ml) and DBU (18.2 ml) were combined at 0° C. under N2 atmosphere, and the mixture was stirred at 0° C. for an hour. Then iodomethane (15.2 ml) was added to the solution at 0° C. The reaction mixture was stirred at r.t. for 3 hours, and poured into 1N—HCl. The mixture was extracted with AcOEt (twice). The combined organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with CHCl3/AcOEt (30:1) as an eluent, and triturated with IPE/n-Hexane to give methyl 2-oxo-3-phenylpropanoate (11.2 g) as a pale yellow wax.

1. customwere combined at 0° C. under N2 atmosphere
2. stirringThe reaction mixture was stirred at r.t. for 3 hours
3. extractionThe mixture was extracted with AcOEt (twice)
4. washThe combined organic layer was washed with brine
5. dry with materialdried over anhydrous MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash column chromatography over silica gel with CHCl3/AcOEt (30:1) as an eluent
8. customtriturated with IPE/n-Hexane

ORD record

ord-50526a2344d44d6db4cf0d891224deb9

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442715B2