Lithium Chloride → 16alpha-Allyloxy-21-chloro-11beta,17-dihydroxypregn-4-ene-3,20-dione

HRID 918413Notes

Reaction equation

HRID 918413 reaction equation
[CH2:1]([O:4][C@@H:5]1[CH2:25][C@@H:24]2[C@:11]([CH3:29])([CH2:12][C@H:13]([OH:28])[C@H:14]3[C@H:23]2[CH2:22][CH2:21][C:20]2[C@:15]3([CH3:27])[CH2:16][CH2:17][C:18](=[O:26])[CH:19]=2)[C@@:6]1([OH:30])[C:7](=[O:10])[CH2:8]O)[CH:2]=[CH2:3].[Cl-:31].[Li+]>CN(C)C=O.O>[CH2:1]([O:4][C@@H:5]1[CH2:25][C@@H:24]2[C@:11]([CH3:29])([CH2:12][C@H:13]([OH:28])[C@H:14]3[C@H:23]2[CH2:22][CH2:21][C:20]2[C@:15]3([CH3:27])[CH2:16][CH2:17][C:18](=[O:26])[CH:19]=2)[C@@:6]1([OH:30])[C:7](=[O:10])[CH2:8][Cl:31])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 6814270016alpha-Allyloxy-11beta,17,21-trihydroxypregn-4-ene-3,20-dione

Product 1

HCID 8673375816alpha-Allyloxy-21-chloro-11beta,17-dihydroxypregn-4-ene-3,20-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 16α-allyloxy-11β,17,21-trihydroxypregn-4-ene-3,20-dione, 21-methanesulfonate (4.6 mmoles) in 60 ml of dimethylformamide is refluxed for 1 hour under nitrogen with 5 g of lithium chloride. The solution is cooled, diluted with water and filtered. The solid is dissolved in chloroform, washed with 5% hydrochloric acid, water, dried, and evaporated in vacuo to yield the title compound.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. dissolutionThe solid is dissolved in chloroform
  4. washwashed with 5% hydrochloric acid, water
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-79021aae87324b95954e1d69ef5b21f0
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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