p-Toluenesulfonic acid → 1alpha,2alpha-Epoxy-3beta,7alpha-dihydroxypregn-5-ene-20-carbaldehyde

HRID 1708769ノート

反応式

HRID 1708769 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]([CH2:18][C@@H:19]([OH:30])[C@@H:20]5[O:29][C@@H:21]53)=[CH:16][C@H:15]4[OH:31])[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]1[C@H:20]2[C@H:19]([OH:30])[CH2:18][C:17]3[C@:22]([CH3:23])([C@@H:21]12)[C@@H:24]1[C@H:14]([C@H:13]2[C@:27]([CH3:28])([CH2:26][CH2:25]1)[C@@H:10]([CH:8]([CH:5]=[O:4])[CH3:9])[CH2:11][CH2:12]2)[C@H:15]([OH:31])[CH:16]=3

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 21226206Ethyl acetate hexaneHCID 8674580820-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregn-5-ene-3beta,7alpha-diol

生成物 1

HCID 867458101alpha,2alpha-Epoxy-3beta,7alpha-dihydroxypregn-5-ene-20-carbaldehyde収率 67%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

In 2.5 ml of acetone was dissolved 2.2 mg (0.005 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregn-5-ene-3β,7α-diol, followed by addition of 0.5 ml of a 1 mmol/1 solution of p-toluenesulfonic acid in acetone (containing 0.0005 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 methylene chloride was added to the residue. This methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate 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 1.2 mg of 1α,2α-epoxy- 3β,7α-dihydroxypregna-5-ene-20-carbaldehyde (yield: 67%).

後処理

  1. customFrom the reaction mixture thus obtained
  2. distillationthe solvent was distilled off under reduced pressure and methylene chloride
  3. additionwas added to the residue
  4. washThis methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate 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-1049bcfd56ee4c5ea2275c3937024b76
出典データセット
uspto-grants-1994_10
特許番号
US05359055

反応ノート

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