Hydrochloric Acid → 9-Hydroxypregn-4-ene-3,20-dione

HRID 1613982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613982
[N+](C(=[C:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@:19]([OH:24])([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C:14]4(OCC[O:25]4)[CH2:15][CH2:16]2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1)C)#[C-].Cl.O.[CH2:31]([O:33]CC)[CH3:32]>O1CCCC1.[OH-].[Na+]>[OH:24][C@:19]12[CH2:9][CH2:8][C@@:22]3([CH3:23])[C@@H:21]([CH2:7][CH2:6][C@@H:5]3[C:31](=[O:33])[CH3:32])[C@@H:20]1[CH2:10][CH2:11][C:12]1[C@:17]2([CH3:18])[CH2:16][CH2:15][C:14](=[O:25])[CH:13]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 5698545720-Isocyano-3,3-ethylenedioxypregna-5,17(20)-dien-9alpha-ol

Produkt 1

HCID 131887039-Hydroxypregn-4-ene-3,20-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 20-isocyano-3,3-ethylenedioxypregna-5,17(20)-dien-9α-ol (2.30 g) in a mixture of tetrahydrofuran (60 ml) and aqueous 2N hydrochloric acid (20 ml) was refluxed for 1 hour. The reaction mixture was cooled to room temperature after which water (25 ml) and diethyl ether (100 ml) were added. The mixture was neutralised with IN sodium hydroxide solution. After separating the layers the aqueous phase was extracted twice with diethyl ether (50 ml). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford 2.02 g of the title compound.

Aufarbeitung

  1. temperaturewas refluxed for 1 hour
  2. additionwere added
  3. customAfter separating the layers the aqueous phase
  4. extractionwas extracted twice with diethyl ether (50 ml)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f13ac462c06a4fdbb78aed308a551fdd
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194602

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