Isopropanol → HCID 15747000, compound

HRID 1492097Notes

Reaction equation

HRID 1492097 reaction equation
[C:1]([O:4][C@H:5]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:7]([CH2:8][CH2:9][C:10]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C:11]=3[C:12](=[O:30])[CH2:13][C@@H:14]2[C@H:15]([CH3:20])[CH2:16][CH2:17][CH2:18][OH:19])[CH2:6]1)(=[O:3])[CH3:2].CC(C)=[O:33].OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O>[C:1]([O:4][C@H:5]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:7]([CH2:8][CH2:9][C:10]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C:11]=3[C:12](=[O:30])[CH2:13][C@@H:14]2[C@H:15]([CH3:20])[CH2:16][CH2:17][C:18]([OH:33])=[O:19])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 15125792HCID 15125792, compoundHCID 131709961Jones' reagent

Product 1

HCID 15747000HCID 15747000, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 3β-acetoxy-24-hydroxy-5α-chol-8(14)-en-15-one (1.0 g) in acetone (50 ml) an 8N solution of Jones reagent was added dropwise with stirring at room temperature until the orange color of the reagent persisted. 2-Propanol (1 ml) was added, and the reaction mixture was filtered through a sintered glass filter and evaporated to dryness under reduced pressure. The residue was dissolved in ethyl acetate, and the organic solution was washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to give 3β-acetoxy-15-keto-5α-chol-8(14)-en-24-oic acid (1.0 g) of over 98% purity as judged by 1H NMR. The product showed single component on TLC in three solvent systems (20% methanol in CHCl3, Rf 0.64; isooctaneethyl acetate-acetic acid 5:5:1, Rf 0.56; and CHCl3 -acetonemethanol 7:5:1, Rf 0.18. The structure was confirmed by I.R, N.M.R., and M.S. analyses.

Workup

  1. filtrationthe reaction mixture was filtered through a sintered glass
  2. filtrationfilter
  3. customevaporated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5ccc4030348d4e1ba6574347d93e934a
Source dataset
uspto-grants-1994_12
Patent number
US05371077

Reaction notes

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