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

HRID 1779523ノート

反応式

HRID 1779523 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 1361364155-Hydroxy-7-isopropoxy-2-methylthiochromone収率 88.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6f74120dd3b54cafa5108e45c7144b1d
出典データセット
uspto-grants-1997_05
特許番号
US05627204

反応ノート

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