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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Pregna-1,4,20-trien-3-one

HRID 1108450
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1108450
[CH2:1]=[CH:2][C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C:10](=[CH:11][C:12](=[O:22])[CH2:13][CH2:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1.CCOCC>[CH2:1]=[CH:2][C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C:10](=[CH:11][C:12](=[O:22])[CH:13]=[CH:14]2)[CH2:9][CH2:8]3)[CH2:5][CH2:4]1
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Komponenten

5

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15429659Pregna-4,20-dien-3-one

Produkt 1

HCID 13034987Pregna-1,4,20-trien-3-oneAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Pregna-4,20-dien-3-one (1, 1.19 g. 3.99 mmol) was refluxed for 24 h with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 2.72 g, 12.1 mmol) in 40 ml of benzene under Argon. The cooled suspension was diluted with ether and washed with two 100 ml portions of 5% (w/w) sodium hydroxide, two 100 ml portions of water and once with 100 ml of brine. Ether (100 ml) was added to the resulting emulsion, which was dried over sodium sulfate and then filtered through a column of sodium sulfate (20 g). After washing the residue twice with 50 ml portions of ether the combined filtrates were concentrated under reduced pressure and then flash chromatographed (25% ethyl acetate/hexanes on silica gel) to give a slightly yellow crystalline solid (0.26 g, 0.88 mmol, 22%).

Aufarbeitung

  1. washwashed with two 100 ml portions of 5% (w/w) sodium hydroxide, two 100 ml portions of water and once with 100 ml of brine
  2. additionEther (100 ml) was added to the resulting emulsion, which
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered through a column of sodium sulfate (20 g)
  5. washAfter washing the residue twice with 50 ml portions of ether the combined filtrates
  6. concentrationwere concentrated under reduced pressure
  7. customflash chromatographed (25% ethyl acetate/hexanes on silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-3bb9bfced1c2410f8ca717dcf4864997
Quelldatensatz
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06066627

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