Testosterone → HCID 70488595, compound

HRID 371191Notes

Reaction equation

HRID 371191 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.[I-:22].[Li+:23]>C1(C)C=CC=CC=1.C(Cl)Cl.CCOCC.O>[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.[I-:22].[Li+:23]

Participants

7

Reactant 2

HCID 6013TestosteroneHCID 66321Lithium iodide

Product 1

HCID 70488595HCID 70488595, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution containing 14.7 g of testosterone in 140 ml of toluene, 65 ml methylene chloride, 25 ml of ether and 2.0 ml of water is added 13.65 g of lithium iodide and the resulting mixture is stirred for 2 hours. To aid in filtration of the mixture 160 ml toluene and 50 ml ether is added. The solids are removed by filtration and washed with 2×50 ml of cold wash solution (4:1, hexane:methylene chloride) followed by 100 ml of hexane. The solids are dried `in vacuo` for 16 hours, then under high vacuum for 24 hours to yield 31.73 g of testosterone lithium iodide complex.

Workup

  1. filtrationTo aid in filtration of the mixture 160 ml toluene and 50 ml ether
  2. additionis added
  3. customThe solids are removed by filtration
  4. washwashed with 2×50 ml of cold wash solution (4:1, hexane:methylene chloride)
  5. customThe solids are dried `in vacuo` for 16 hours
  6. customunder high vacuum for 24 hours to yield 31.73 g of testosterone lithium iodide complex

Sources & evidence

ORD record
ord-d361e7373c6546caa3b23983c83fd51a
Source dataset
uspto-grants-1985_07
Patent number
US04529811

Reaction notes

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