Dichloromethane → HCID 68730766, compound

HRID 1182880Notes

Reaction equation

HRID 1182880 reaction equation
[OH:1][C@@H:2]1[C:19]2[C@:14]([CH3:23])([CH2:15][CH2:16][C:17](=[O:22])[C:18]=2[CH2:20][CH3:21])[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([O:24][C:25](=[O:27])[CH3:26])[CH2:7][CH2:6]3)[CH2:3]1.O[C@H]1C2[C@](C)(CCC(=O)C=2CC)[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)[C@@H](OC(=O)C)CC3)C1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(Cl)Cl>CC(C)=O>[C:25]([O:24][C@H:8]1[CH2:7][CH2:6][C@H:5]2[C@H:4]3[C@H:13]([CH2:12][CH2:11][C@:9]12[CH3:10])[C@:14]1([CH3:23])[C:19](=[C:18]([CH2:20][CH3:21])[C:17](=[O:22])[CH2:16][CH2:15]1)[C:2](=[O:1])[CH2:3]3)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 68732269HCID 68732269, compoundHCID 68733032HCID 68733032, compoundHCID 131709961Jones' reagent

Product 1

HCID 68730766HCID 68730766, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of a 6α-hydroxy-17β-acetoxy-4-ethylandrost-4-en-3-one and 6β-hydroxy-17β-acetoxy-4-ethylandrost-4-en-3-one (510 mg) in acetone (34 ml) cooled at 0° C., Jones reagent (1.1 ml) was added dropwise. 5 min after completion of the addition, DCM (140 ml) was added and the mixture was washed with 10% Na2SO3 aqueous solution, 5% aqueous NaHCO3 solution, and brine. The organic phase was dried over Na2SO4, and evaporated to dryness to give 17β-acetoxy-4-ethylandrost-4-en-3,6-dione (465 g, 92%).

Workup

  1. additionwas added
  2. washthe mixture was washed with 10% Na2SO3 aqueous solution, 5% aqueous NaHCO3 solution, and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-2dbd1bdd24d346aca9eaa484a11e5e0c
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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