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

HRID 371845Notes

Reaction equation

HRID 371845 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 1,5-androstadiene-3β,17β-diol in a mixture of dry ether and glyme is added zinc-copper couple and methylene iodide. This reaction mixture is refluxed for 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 crystallized from acetone-hexane to yield 1β,2β-methylene-5-androstene-3β,17β-diol.

Workup

  1. temperatureThis reaction mixture is refluxed for 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 crystallized from acetone-hexane

Sources & evidence

ORD record
ord-be0e67c0ec254ac7830b8eab21d1c9e3
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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