Iodine → HCID 22856669, compound

HRID 1720773Notes

Reaction equation

HRID 1720773 reaction equation
[CH3:1][C@@H:2]1[CH2:21][C@@H:20]2[C@:7]([CH3:24])([CH2:8][CH2:9][C@H:10]3[C@H:19]2[CH2:18][CH2:17][C:16]2[C@:11]3([CH3:23])[CH:12]=[CH:13][C:14](=[O:22])[CH:15]=2)[C@H:3]1[C:4](=[O:6])[CH3:5].[Cl-].[Ca+2].[Cl-].[O-2].[Ca+2].[I:30]I>CO.C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[I:30][CH2:5][C:4](=[O:6])[C@@H:3]1[C@:7]2([CH3:24])[C@H:20]([C@H:19]3[C@H:10]([CH2:9][CH2:8]2)[C@:11]2([CH3:23])[C:16](=[CH:15][C:14](=[O:22])[CH:13]=[CH:12]2)[CH2:17][CH2:18]3)[CH2:21][C@H:2]1[CH3:1]

Participants

8

Reactant 4

HCID 807IodineHCID 5284359Calcium Chloride2×HCID 6850728CalciumoxideHCID 54339148HCID 54339148, compound

Product 1

HCID 22856669HCID 22856669, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent3×HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

16α-Methylpregna-1,4-diene-3,20-dione (2.26 g), carbon tetrachloride (15 ml), methanol (7.3 ml) and calcium chloride in methanol (10%, 0.24 ml) are combined and stirred for 15 min at 20°-25°. Calcium oxide (2.50 g) is added and the mixture stirred an additional 5 min. A mixture of iodine (3.54 g), calcium chloride (10%, 5.4 ml) and methanol (2.4 ml) is added dropwise over 1 hr to the steroid mixture. After an additional 30 min the mixture is diluted with methylene chloride (100 ml), filtered through celite and concentrated. The residue is partitioned between methylene chloride and water, the phases are separated, the organic phase is washed with sodium sulfite, dried over magnesium sulfate and then concentrated to give the title compound, NMR (CDCl3) 0.7, 0.9, 1.2, 5.25, 5.35, 6.0, 6.2 and 7.0 δ.

Workup

  1. stirringthe mixture stirred an additional 5 min
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe residue is partitioned between methylene chloride and water
  5. customthe phases are separated
  6. washthe organic phase is washed with sodium sulfite
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-87204a33bb09410f9c0b46e73583c56b
Source dataset
uspto-grants-1996_04
Patent number
US05506354

Reaction notes

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