Water → 9-Dehydro-progesterone

HRID 1613983Notes

Reaction equation

HRID 1613983 reaction equation
O[C@:2]12[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C:16](=[O:18])[CH3:17])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH2:4][CH2:5][C:6](=[O:23])[CH:7]=1.O.C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:17][C:16](=[O:18])[C@@H:15]1[C@:19]2([CH3:22])[C@H:12]([C@H:11]3[C:2](=[CH:21][CH2:20]2)[C@:3]2([CH3:24])[C:8](=[CH:7][C:6](=[O:23])[CH2:5][CH2:4]2)[CH2:9][CH2:10]3)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 131887039-Hydroxypregn-4-ene-3,20-dione

Product 1

HCID 119661839-Dehydro-progesterone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 9α-hydroxypregn-4-ene-3,20-dione (218 mg) in 70% (v/v) aqueous sulfuric acid was stirred at room temperature for 1 hour after which the reaction mixture was added dropwise to a stirred mixture of water (5 ml) and ethyl acetate (5 ml). The organic layer was washed with a 5% aqueous potassium carbonate solution, then with water to neutral pH, dried (MgSO4) and concentrated under reduced pressure. The crude product (149 mg), still containing some starting material, was purified by chromatography (silica gel, toluene/acetone 3/1) to afford the title compound.

Workup

  1. washThe organic layer was washed with a 5% aqueous potassium carbonate solution
  2. dry with materialwith water to neutral pH, dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. additionThe crude product (149 mg), still containing some starting material
  5. customwas purified by chromatography (silica gel, toluene/acetone 3/1)

Sources & evidence

ORD record
ord-4cc3b43d08f445d69d3c11291a104113
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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