p-Toluenesulfonic acid → 3-Oxopregna-1,4,6-triene-20-carbaldehyde

HRID 1196329ノート

反応式

HRID 1196329 の反応式
CC1(C)CO[CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17](=[CH:18][C:19](=[O:29])[CH:20]=[CH:21]3)[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:4]C1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>CC(C)=O>[O:29]=[C:19]1[CH:20]=[CH:21][C@@:22]2([CH3:23])[C:17]([CH:16]=[CH:15][C@@H:14]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[CH:8]([CH:5]=[O:4])[CH3:9])=[CH:18]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 21226206Ethyl acetate hexaneHCID 2284393220-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one

生成物 1

HCID 228438853-Oxopregna-1,4,6-triene-20-carbaldehyde収率 75%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

In 100 ml of acetone was dissolved 0.410 g (1.0 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one, followed by addition of 10 mg (0.05 mmole) of p-toluenesulfonic acid. The mixture was stirred at room temperature for 12 hours. From the reaction mixture thus obtained, the solvent was distilled off under reduced pressure and the residue was diluted with methylene chloride. The methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:5, v/v) to recover 0.243 g of 3-oxopregna-1,4,6-triene-20-carbaldehyde (yield: 75%).

後処理

  1. customFrom the reaction mixture thus obtained
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionthe residue was diluted with methylene chloride
  4. washThe methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography (eluent

出典と根拠

ORDレコード
ord-ccdd53005fa744c4b8547bbbda92811a
出典データセット
uspto-grants-1992_05
特許番号
US05112998

反応ノート

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