Phenol → 4-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

HRID 642303

反応式

HRID 642303 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 576654844-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester収率 66.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
95 °C

実験手順

A mixture of 2-bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester (1.89 g, 7.57 mmol), phenol (855 mg, 9.09 mmol) and potassium carbonate (1.36 g, 9.84 mmol) in dimethylformamide (18 mL) was heated at 95° C. for 15 h before it was cooled to room temperature and partitioned between ethyl acetate and water, the organic layer was washed with water, aqueous sodium hydroxide (2×), brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow oil (1.32 g): MS: (+) m/z 264.0 (M+1).

後処理

  1. temperaturewas cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washthe organic layer was washed with water, aqueous sodium hydroxide (2×), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-b411f471c03a45d58a8b812d8bf98bcb
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

関連ノート

読み込み中…