Dimethylformamide → 5-Hydroxy-7-isopropoxy-2-methylthiochromone

HRID 1779523노트

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HRID 1779523 반응식
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2.C(=O)([O-])[O-].[K+].[K+].[CH:21](I)([CH3:23])[CH3:22].CN(C=O)C>O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:21]([CH3:23])[CH3:22])[CH:9]=[C:8]2[C:3]=1[C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1361024115,7-Dihydroxy-2-methylthiochromone

생성물 1

HCID 1361364155-Hydroxy-7-isopropoxy-2-methylthiochromone수율 88.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

A mixture consisting of 6.88 g (30.35 mmol) 5,7-dihydroxy-2-methylthiochromone, 12.56 g (91.05 mmol) potassium carbonate, 6.07 ml (60.70 mmol) isopropyl iodide, and 150 ml DMF was stirred at 60° C. for 30 min. Subsequently, water was added to the solution. The product was extracted twice with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled out under reduced pressure. The resulting crude product was purified by flash column chromatography (hexane ethyl acetate=4:1), whereby 6.71 g of 5-hydroxy-7-isopropoxy-2-methylthiochromone was obtained (yield: 83%).

후처리

  1. extractionThe product was extracted twice with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled out under reduced pressure
  5. customThe resulting crude product was purified by flash column chromatography (hexane ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-6f74120dd3b54cafa5108e45c7144b1d
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05627204

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