HCID 46179967, compound → HCID 25235420, compound

HRID 1527673Notes

Reaction equation

HRID 1527673 reaction equation
[Cl:1][C:2]1[C:7]([O:8]C)=[C:6]([O:10][CH3:11])[C:5]([O:12][CH3:13])=[C:4]([O:14]C)[C:3]=1/[CH:16]=[C:17](\[CH3:21])/[C:18]([OH:20])=[O:19]>C(#N)C.O>[Cl:1][C:2]1[C:7](=[O:8])[C:6]([O:10][CH3:11])=[C:5]([O:12][CH3:13])[C:4](=[O:14])[C:3]=1/[CH:16]=[C:17](\[CH3:21])/[C:18]([OH:20])=[O:19]

Participants

4

Reactant 1

HCID 46179967HCID 46179967, compound

Product 1

HCID 25235420HCID 25235420, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Following a modified procedure of Flader et al.,22 22 (0.124 g, 0.391 mmol) was dissolved in acetonitrile (10.0 mL) at room temperature, then ceric ammonium nitrate (0.970 g, 1.77 mmol) dissolved in water (8.0 ml) was added at room temperature. The reaction was stirred for 30 minutes and then extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4, filtered, and condensed. The red oil was then purified by either flash column chromatography (1:1 Et2O:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes to afford 23 (0.026 g, 0.091 mmol, 22%) as a red solid.

Workup

  1. additionwas added at room temperature
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customcondensed
  7. customThe red oil was then purified by either flash column chromatography (1:1 Et2O:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes

Sources & evidence

ORD record
ord-89bcb09b24cb4c06bcef67e145dde6c7
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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