Water → 1-[2-(Benzyloxy)phenyl]ethan-1-one

Temperature

0 °C

To a cold (0° C.) solution of 3-benzyloxypicolinonitrile (2.50 g, 11.9 mmol) in tetrahydrofuran (100 mL) was added dropwise 0.92M methyl magnesium bromide in tetrahydrofuran (150 mL, 138 mmol). The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hrs. The reaction mixture was poured into water (2000 mL) and acidified with 10% sulfuric acid (500 mL). After being stirred for 30 min, the reaction mixture was poured into saturate aqueous NaHCO3 solution slowly and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, filtrated, and evaporated. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/3) to give 1-(2-benzyloxyphenyl)-ethanone as a colorless oil (2.49 g, yield; 92%).

1. waitat room temperature for 4 hrs
2. stirringAfter being stirred for 30 min
3. additionthe reaction mixture was poured
4. concentrationinto saturate aqueous NaHCO3 solution slowly
5. extractionextracted with ethyl acetate
6. washThe organic phase was washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltrated
9. customevaporated
10. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/3)

ORD record

ord-483d449854bf487c9f883657dec4d9ad

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435743B2