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Water → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one

HRID 1196312
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1196312
[CH3:1][C:2]1([CH3:31])[CH2:7][O:6][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)[CH2:16][C@H:15]4O)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)(=O)C.CCCCCC>C1C=CC=CC=1>[CH3:31][C:2]1([CH3:1])[CH2:3][O:4][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:6][CH2:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 21226206Ethyl acetate hexaneHCID 2284393020-(5,5-Dimethyl-1,3-dioxan-2-yl)-7alpha-hydroxypregna-1,4-dien-3one

Produkt 1

HCID 2284393220-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of 3.00 g (6.98 mmoles) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-7α-hydroxypregna-1,4-dien-3-one in 200 ml of benzene was added 50 mg of p-toluenesulfonic acid and the mixture was refluxed for 5 hours, with the byproduct water being constantly removed from the reaction system by means of a Dean-Stark trap. The reaction mixture thus obtained was cooled to room temperature and washed with aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with ether and the extract was combined with the organic layer. This mixture was washed with aqueous sodium chloride solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane =1:10, v/v) to recover 2.58 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one (yield: 90%). The 1H-NMR spectrum of this product was in agreement with that of the 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-1,4,6-trien-3-one obtained in Example 3.

Aufarbeitung

  1. customconstantly removed from the reaction system by means of a Dean-Stark trap
  2. customThe reaction mixture thus obtained
  3. washwashed with aqueous sodium hydrogen carbonate solution
  4. extractionThe aqueous layer was extracted with ether
  5. washThis mixture was washed with aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customFinally the residue was purified by silica gel chromatography (eluent

Quellen und Nachweise

ORD-Eintrag
ord-5bccbcc13aa7416f993ef0149b736694
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05112998

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