Carbon Dioxide → 3-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one

5-Hydroxy-2-methyl-1H-pyridin-4-one hydrochloride (1.00 g, 6.19 mmol) and potassium carbonate (1.02 g, 7.42 mmol) was mixed together in water (10 mL) at room temperature, and stirred until evolution of carbon dioxide ceased. Then, 2,2,2-trifluoro-1-methoxy-ethanol (1.60 g, 12.4 mmol) was added. The reaction mixture was heated in a sealed flask at 100.degree. C. for 20 h. The mixture was cooled down to RT and neutralized with acetic acid to pH at between 5 to 6. The precipitate was collected by suction filtration and washed with water and ether. Thus, 3-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one was obtained as an off-white solid (1.06 g, 76% yield). 1H NMR (90 MHz, DMSO-d6) δ (ppm): 6.09 (s, 1H, CH); 5.42 (apparent q, 1H, CH), 2.28 (s, 3H, CH3); MS-ESI (m/z) 224.1 [M+1]+, 206.1, 186.1, 178.1.

1. temperatureThe reaction mixture was heated in a sealed flask at 100.degree
2. filtrationThe precipitate was collected by suction filtration
3. washwashed with water and ether

ORD record

ord-1c57b5b7bae44642a79a4332b6b8f588

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673943B2