Potassium Carbonate → 1-Acetoxy-16alpha-chloro-3-methoxyestra-1,3,5(10)-trien-17-one

HRID 839754Notes

Reaction equation

HRID 839754 reaction equation
[Cl:1]Cl.[C:3]([O:6][C:7]1[C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18]([O:25]C(=O)C)=[CH:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([O:29][CH3:30])[CH:8]=1)(=[O:5])[CH3:4].C([O-])([O-])=O.[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[C:3]([O:6][C:7]1[C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:25])[C@H:17]([Cl:1])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([O:29][CH3:30])[CH:8]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 24526ChlorineHCID 545479651,17-Diacetoxy-3-methoxyestra-1,3,5(10),16-tetraene

Product 1

HCID 706143801-Acetoxy-16alpha-chloro-3-methoxyestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of Cl2 (0.162 g, 2.3 mM) in 5 ml of carbon tetrachloride is added over a period of 30 min to a stirred suspension of 1,17-diacetoxy-3-methoxyestra-1,3,5(10),16-tetraene (0.77 g, 2 mM), K2CO3 (5 g) and 25 ml of CCl4 at 0°. Dilute aqueous sodium thiosulfate is then added, the layers are separated and the aqueous layer is extracted with 2 × 50 ml chloroform. The organic layers are combined, dried over MgSO4 and evaporated in vacuo. The residue is triturated with ether to give a white solid. Recrystallization from methanol gives 1-acetoxy-16α-chloro-3-methoxyestra-1,3,5(10)-trien-17-one, yield 0.64 g (76%); m.p. 194.5°-196°.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted with 2 × 50 ml chloroform
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue is triturated with ether
  6. customto give a white solid
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e60f6ab646bc4faea18baa56956cf2de
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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