HCID 90035345, compound → HCID 118253186, compound

HRID 1776960Notes

Reaction equation

HRID 1776960 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([O:10]C)=[CH:5][C:4]=1[CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17]>C(#N)C.O>[CH3:9][C:7]1[C:6](=[O:10])[CH:5]=[C:4]([CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:3](=[O:2])[CH:8]=1

Participants

4

Reactant 1

HCID 90035345HCID 90035345, compound

Product 1

HCID 118253186HCID 118253186, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5 (1.26 g, 4.99 mmol) in acetonitrile (15 cm3) was added ceric ammonium nitrate (5.50 g, 9.99 mmol) in water (10 cm3) dropwise. The mixture was stirred for 1 hr before the organics were extracted with dichloromethane (3×25 cm3), washed with brine (25 cm3), dried (MgSO4) and concentrated under vacuum to yield the title compound as a brown oil 6 (756 mg, 68%).

Workup

  1. extractionorganics were extracted with dichloromethane (3×25 cm3)
  2. washwashed with brine (25 cm3)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-be896b8b0a3845c58d219ee2cc71c6d8
Source dataset
uspto-grants-2016_02
Patent number
US09266829B2

Reaction notes

Loading…