HCID 21705598, compound → HCID 10913048, compound

HRID 1596054Notes

Reaction equation

HRID 1596054 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16].CC(C)=[O:23].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:18]([O:17][C:15]([C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[CH2:4][CH2:3][C:2]([OH:23])=[O:1])=[O:16])[CH:19]=[CH2:20]

Participants

4

Reactant 2

HCID 21705598HCID 21705598, compoundHCID 131709961Jones' reagent

Product 1

HCID 10913048HCID 10913048, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Example 11B (1.4 g, 5.18 mmol) in acetone (20 mL) was treated with Jones reagent (CrO3/H2SO4) until the orange color persisted, quenched with isopropyl alcohol, partitioned between ethyl acetate and water. The organic layer was washed with water, dried (Na2SO4), filtered, concentrated, and purified on silica gel with a gradient of 30% ethyl acetate/hexanes to 10% MeOH/dichloromethane to provide 1.27 g (86%) of the desired compound as an yellow oil.

Workup

  1. customquenched with isopropyl alcohol
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel with a gradient of 30% ethyl acetate/hexanes to 10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-a43a76e519cd4d3f895d20e8a169a2c4
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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