Lithium Hydroxide → 2-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid

HRID 1260322ノート

反応式

HRID 1260322 の反応式
C[O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:7][CH:6]=1)=[O:4].[OH-].[Li+].ClCCl>C1COCC1.CO>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=1

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 57688443Methyl 2-(pyridin-2-yl)thiazole-5-carboxylate

生成物 1

HCID 232838552-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid収率 93.9%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

2-Pyridin-2-yl-thiazol-5-carboxylic acid methyl ester (0.34 g, 1.55 mmol) was dissolved in a THF/methanol (5 ml/1 ml) mixture, cooled to 0° C. and treated with lithium hydroxide (4.7 ml, 1N aqueous solution). The reaction mixture was allowed to warm-up to ambient temperature, stirred at that temperature for 30 min and the pH value was subsequently adjusted to ˜5. The resulting suspension was treated with dichloromethane (50 ml) and filtered. The precipitate was washed with water and dichloromethane, the filtrate was extracted with dichloromethane. The combined organic phases were dried, evaporated and combined with the precipitate to yield the product as light brown solid (0.3 g, 92%). MS: M=161.1 (M-CO2—H)−

後処理

  1. temperatureto warm-up to ambient temperature
  2. filtrationfiltered
  3. washThe precipitate was washed with water and dichloromethane
  4. extractionthe filtrate was extracted with dichloromethane
  5. customThe combined organic phases were dried
  6. customevaporated

出典と根拠

ORDレコード
ord-2b032ecaf5f24dff94b6e06c1c1b144d
出典データセット
uspto-grants-2013_06
特許番号
US08470820B2

反応ノート

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