Dimethyl Sulfoxide → 2-cyclopropylthiazole-4-carbaldehyde

To a solution of 4-(chloromethyl)-2-cyclopropylthiazole (3.0 g, 17.2 mmol) in DMSO (10 mL) was charged MnO2 (1.5 g, 17.2 mmol). The mixture was heated to 100° C. overnight, cooled to room temperature and diluted with EtOAc (30 mL). The mixture was filtered through Celite and washed with EtOAc (3×30 mL). The combined organic layer was washed with brine (3×40 mL) and concentrated. The residue was purified by silica gel chromatography using 2 to 5% EtOAc in hexane to afford the title compound (1.0 g, 38%) as a light brown oil, which solidified upon standing in a refrigerator overnight. 1H NMR (400 MHz, CDCl3) δ 9.91 (s, 1H), 7.93 (s, 1H), 2.36 (m, 1H), 1.20 (m, 2H), 1.16 (m, 2H). MS (ES) m/z 154.1 (M+H+).

1. temperaturecooled to room temperature
2. filtrationThe mixture was filtered through Celite
3. washwashed with EtOAc (3×30 mL)
4. washThe combined organic layer was washed with brine (3×40 mL)
5. concentrationconcentrated
6. customThe residue was purified by silica gel chromatography

ORD-Eintrag

ord-9058fec120884a6690966e36be8d8dbd

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853202B2