Carbon Dioxide → 3-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one
Reaction equation
Cl.[OH:2][C:3]1[C:4](=[O:10])[CH:5]=[C:6]([CH3:9])[NH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)=O.[F:20][C:21]([F:27])([F:26])[CH:22](OC)[OH:23]>O.C(O)(=O)C>[OH:2][C:3]1[C:4](=[O:10])[CH:5]=[C:6]([CH3:9])[NH:7][C:8]=1[CH:22]([OH:23])[C:21]([F:27])([F:26])[F:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
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° 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.
Workup
- filtrationThe precipitate was collected by suction filtration
- washwashed with water and ether
Sources & evidence
- ORD record
- ord-7b1e6d08f0f8468cbe07850641faef23
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026261B2
Reaction notes
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