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

HRID 1708762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708762
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4987a94af035478fa2b499315b055c94
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05359055

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