Water → 3-(2-Oxopropyl)tetrahydro-4H-pyran-4-one

(3,6-dihydro-2H-pyran-4-yloxy)trimethylsilane (1.0 g, 5.80 mmol) and trimethyl(prop-1-en-2-yloxy)silane (7.56 g, 58.0 mmol) were added dropwise to a vigorously stirred suspension of ceric ammonium nitrate (6.36 g, 11.61 mmol) and sodium bicarbonate (1.950 g, 23.22 mmol) in dry acetonitrile (40 ml). The resulting mixture was stirred until the orange color disappeared and a thick white precipitate formed. The reaction mixture was then poured into water and extracted with EtOAc. The combined extracts were washed by brine, and dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel, using EtOAc/Hex 10-50% to give the product (0.42 g, 46.3% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 4.30-4.25 (m, 1H), 4.21-4.16 (m, 1H), 3.68-3.62 (m, 1H), 3.37-3.31 (m, 1H), 3.19-3.15 (m, 1H), 2.91-2.85 (m, 1H), 2.75-2.66 (m, 1H), 2.39-2.34 (m, 1H), 2.21-2.15 (m, 4H).

1. customa thick white precipitate formed
2. extractionextracted with EtOAc
3. washThe combined extracts were washed by brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe residue was purified by column chromatography on silica gel

ORD record

ord-87c613b42b8c42789cd7c9af92794cad

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674115B2