Diiodomethane → 1beta,2beta-Methylene-5-androstene-3beta,17beta-diol

HRID 2397985Notes

Reaction equation

HRID 2397985 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21].[CH2:22](COC)OC.C(I)I>CCOCC.[Cu].[Zn]>[CH2:22]1[C@@H:13]2[C@H:12]([OH:20])[CH2:11][C:10]3[C@:15]([CH3:16])([C@H:14]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[C@@H:3]([OH:21])[CH2:4][CH2:5]2)[CH2:8][CH:9]=3

Participants

6

Reactant 3

HCID 6346DiiodomethaneHCID 80711,2-DimethoxyethaneHCID 571202841,5-Androstadiene-3beta,17beta-diol

Product 1

HCID 566286851beta,2beta-Methylene-5-androstene-3beta,17beta-diol

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of the 1,5-androstadiene-3β,17β-diol so prepared in a mixture of dry ether and glyme is added zinc-copper couple and methylene iodide. The mixture is refluxed for a period of about 4 hours, cooled to room temperature, diluted with ether and filtered. The filtrate is washed with an aqueous sodium chloride solution, water and dried over anhydrous magnesium sulfate. The ether is removed under reduced pressure and the residue crystallized from acetone-hexane to yield 1β,2β-methylene-5-androstene-3β,17β-diol.

Workup

  1. temperatureThe mixture is refluxed for a period of about 4 hours
  2. filtrationfiltered
  3. washThe filtrate is washed with an aqueous sodium chloride solution, water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe ether is removed under reduced pressure
  6. customthe residue crystallized from acetone-hexane

Sources & evidence

ORD record
ord-73725ee3d68a49b9a1b69122e86ba259
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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