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

HRID 1834974Notes

Reaction equation

HRID 1834974 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 consisting of 1,5-androstadiene-3β,17β-diol in a mixture of dry ether and glyme is added zinc-copper couple and methylene iodide. This mixture is refluxed for approximately 4 hours, cooled to room temperature, diluted with ether and filtered. The filtrate is washed with aqueous sodium chloride, water and dried over anhydrous magnesium sulfate. The ether is removed under reduced pressure and the residue is crystallized from an acetone-hexane solution to yield 1β,2β-methylene-5-androstene-3β,17β-diol.

Workup

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

Sources & evidence

ORD record
ord-bbed0961d3214144bba16e987572dbdb
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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