Chloroacetone → 6-(2-Methoxyphenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one

HRID 1700471ノート

反応式

HRID 1700471 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH2:12][C:11](=[O:16])[CH2:10]1.[H-].[Na+].Cl[CH2:20][C:21](=O)[CH3:22]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:10][C:11](=[O:16])[C:12]2[C:21]([CH3:22])=[CH:20][O:15][C:13]=2[CH2:14]1

参加物

5

反応物 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 171223135-(2-Methoxyphenyl)-1,3-cyclohexanedione

生成物 1

HCID 183176276-(2-Methoxyphenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-(2-methoxyphenyl)cyclohexane-1,3-dione (mp144-145° C.; 1.09 g) in DMF (15 ml) was added 60% sodium hydride (0.22 g), and the mixture was stirred, under argon atmosphere, at room temperature for 15 minutes. To the mixture was added chloroacetone (0.45 ml), and the mixture was stirred at 150° C. overnight (14 hours). The reaction solution was cooled and concentrated under reduced pressure. To the residue was added ice-water, and the mixture was extracted with ethyl acetate. The upper layer was washed with saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure, and the residue was subjected to silica gel chromatography and eluted with ethyl acetate/hexane to give 6-(2-methoxyphenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.20 g).

後処理

  1. stirringthe mixture was stirred at 150° C. overnight (14 hours)
  2. temperatureThe reaction solution was cooled
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added ice-water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe upper layer was washed with saturated brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. concentrationconcentrated under reduced pressure
  9. washeluted with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-165eebf830d84466bbd060de1354e569
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

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