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

HRID 1613982Notes

Reaction equation

HRID 1613982 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f13ac462c06a4fdbb78aed308a551fdd
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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