HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 371845
Notes
Print preview

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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 coupleCatalyst
HCID 3283
Diethyl Ether
Solvent
2×

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04087524

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes