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

HRID 1404205노트

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HRID 1404205 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3dd6e8fbcc7d4118ad95ad1fc471bf44
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912224B2

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