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

HRID 642303

반응식

HRID 642303 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
95 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b411f471c03a45d58a8b812d8bf98bcb
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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