Potassium Carbonate → 2-(2-o-Tolyl-chroman-6-yloxy)-thiazole-5-carboxylic acid methyl ester

HRID 1404205ノート

反応式

HRID 1404205 の反応式
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[CH:13]=2)[O:8]1.Cl[C:20]1[S:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:28][O:27][C:25]([C:22]1[S:21][C:20]([O:17][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[O:8][CH:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:18])[CH2:16][CH2:15]3)=[N:24][CH:23]=1)=[O:26]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 12897294Methyl 2-chloro-1,3-thiazole-5-carboxylateHCID 712928852-o-Tolyl-chroman-6-ol

生成物 1

HCID 712929632-(2-o-Tolyl-chroman-6-yloxy)-thiazole-5-carboxylic acid methyl ester収率 98%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A suspension of 2-o-Tolyl-chroman-6-ol (2.5 g, 10.4 mmol), methyl 2-chloro-thiazole-5-carboxylate (1.9 g, 10.6 mmol, 1.02 eq) and potassium carbonate (1.9 g, 1.3 eq) in dimethylformamide (30 ml) was stirred at 50° C. for 10 h. The suspension was cooled to room temperature and diluted with water. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with water, dried with sodium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel; ethyl acetate/heptane gradient). The product was obtained as a pale yellow solid (3.87 g, 98%).

後処理

  1. temperatureThe suspension was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers washed with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel; ethyl acetate/heptane gradient)

出典と根拠

ORDレコード
ord-3dd6e8fbcc7d4118ad95ad1fc471bf44
出典データセット
uspto-grants-2014_12
特許番号
US08912224B2

反応ノート

読み込み中…