Isopropanol → HCID 18640504, compound

HRID 1708899Notes

Reaction equation

HRID 1708899 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]2[C@H:16]3[C@H:26]([CH2:27][CH2:28][C@:11]12[CH3:12])[C@:24]1([CH3:25])[C@H:19]([CH:20]=[C:21]([P:29]([O:33][CH3:34])(=[O:32])[O:30][CH3:31])[CH2:22][CH2:23]1)[CH2:18][CH2:17]3)(C(C)(C)C)(C)C.CC(C)=[O:37].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:31][O:30][P:29]([C:21]1[CH2:22][CH2:23][C@@:24]2([CH3:25])[CH:19]([CH2:18][CH2:17][C@@H:16]3[C@@H:26]2[CH2:27][CH2:28][C@@:11]2([CH3:12])[C@H:13]3[CH2:14][CH2:15][C@@H:10]2[C:9]([OH:37])=[O:8])[CH:20]=1)([O:33][CH3:34])=[O:32]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 53876294HCID 53876294, compoundHCID 131709961Jones' reagent

Product 1

HCID 18640504HCID 18640504, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethyl 17β-(t-butyldimethylsilyloxymethyl)-5α-androst-3-ene-3-phosphonate (500 mg), was dissolved in 150 ml acetone. Jones reagent was added until a red color persisted. Isopropanol was then added to quench excess Jones reagent. The acetone was decanted off and the residual chromium salts were then dissolved in water and washed 3 times with dichloromethane. The organic layers were combined and passed through a plug of florosil and concentrated to give 360 mg (99%) of 3-dimethylphosphono-3-androstene-17β-carboxylic acid.

Workup

  1. customto quench excess Jones reagent
  2. customThe acetone was decanted off
  3. dissolutionthe residual chromium salts were then dissolved in water
  4. washwashed 3 times with dichloromethane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cbe108e37e1947b8adacf6cd5f0f80aa
Source dataset
uspto-grants-1990_08
Patent number
US04946834

Reaction notes

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