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

HRID 1187506

反応式

HRID 1187506 の反応式
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]

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 11430Potassium CarbonateHCID 672826585-hydroxy-2-methyl-1H-pyridin-4-one hydrochloride

生成物 1

HCID 250186523-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c57b5b7bae44642a79a4332b6b8f588
出典データセット
uspto-grants-2014_03
特許番号
US08673943B2

関連ノート

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