HCID 19981496, compound → HCID 19981497, compound

HRID 1461140Notes

Reaction equation

HRID 1461140 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH2:12][CH:13]=C)[C:8](=[O:11])[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:22].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:8](=[O:11])[CH2:9][CH3:10])[CH2:12][CH:13]=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 19981496HCID 19981496, compoundHCID 23667635Sodium periodate

Product 1

HCID 19981497HCID 19981497, compoundYield 17.2%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

4,4-diphenyl-6-hepten-3-one (144 mg) was dissolved in a mixture of dioxane and water (3:1, 11 ml). A 10% aqueous osmium tetroxide solution (0.5 ml) was added. The resultant solution was stirred at room temperature for 5 min. A solution of sodium periodate (550 mg) in water was then added dropwise. The reaction mixture was allowed to stir for 16 hours. Water was added, and the aqueous mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water (once) and dried (MgSO4). Rotary evaporation of the solution gave a crude product which was purified by preparative thin layer chromatography (PTLC) on silica gel. Development with hexane/ethyl acetate (2:1) produced three bands. The lowest band (Rf 0.66) was scraped off the plate and eluted with methanol to yield 25 mg of 3,3-diphenyl-4-oxo-hexanal.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with water (once) and
  3. dry with materialdried (MgSO4)
  4. customRotary evaporation of the solution
  5. customgave a crude product which
  6. customwas purified by preparative thin layer chromatography (PTLC) on silica gel
  7. customDevelopment with hexane/ethyl acetate (2:1) produced three bands
  8. washeluted with methanol

Sources & evidence

ORD record
ord-105f015cd92e4c51a6de74b4be00c175
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

Loading…