Acetic Anhydride → 20-(1,3-Dioxolan-2-yl)-3beta-acetoxypregn-6-ene-1alpha,5alpha-diol

HRID 1196362Notes

Reaction equation

HRID 1196362 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C@:15]([OH:29])([CH2:16][C@@H:17]([OH:28])[CH2:18][C@@H:19]2[OH:27])[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C@:15]([OH:29])([CH2:16][C@@H:17]([O:28][C:30](=[O:32])[CH3:31])[CH2:18][C@@H:19]2[OH:27])[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 6785299520-(1,3-Dioxolan-2-yl)pregn-6-ene-1alpha,3beta,5alpha-triol

Product 1

HCID 6785296520-(1,3-Dioxolan-2-yl)-3beta-acetoxypregn-6-ene-1alpha,5alpha-diol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 5 ml of pyridine was dissolved 400 mg of 20-(1,3-dioxolan-2-yl)pregn-6-ene-1α,3β,5α-triol. To this solution was added 0.11 ml of acetic anhydride at a temperature of -10°-0° C. and the mixture was stirred under ice-cooling for 2 hours. The reaction mixture thus obtained was poured in ice-water and stirred at room temperature for 30 minutes. This mixture was then extracted with ether and the extracts were pooled, washed successively with water, cold diluted hydrochloric acid, water, aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution and dried over magnesium sulfate, followed by concentration under reduced pressure. Finally the concentrate was purified by silica gel chromatography to give 420 mg of 20-(1,3-dioxolan-2-yl)-3β-acetoxypregn-6-ene-1α,5α-diol showing the following properties.

Workup

  1. temperaturecooling for 2 hours
  2. customThe reaction mixture thus obtained
  3. stirringstirred at room temperature for 30 minutes
  4. extractionThis mixture was then extracted with ether
  5. washwashed successively with water, cold diluted hydrochloric acid, water, aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationfollowed by concentration under reduced pressure
  8. customFinally the concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-eb749e7ba6cd448481ff30983fcdd7db
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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