Water → HCID 10956203, compound

HRID 2396604Notes

Reaction equation

HRID 2396604 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[CH2:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:20]CC1.S([O-])(O)=O.[Na+].[OH2:29]>C(#N)C.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:20])([C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:15][OH:29])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 15340718HCID 15340718, compound2×HCID 23665763Sodium Bisulfite

Product 1

HCID 10956203HCID 10956203, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

3.0 g of 1-(4-chlorophenyl)-3-methylene-4,4-dimethylpentane prepared as described above (1) was dissolved in a mixture solvent of 40 ml of acetonitrile and 10 ml of water, and 3.2 g of 4-methylmorpholine-N-oxide was added thereto. After addition of 10 ml of a 4% aqueous solution of osmium tetroxide, the mixture was stirred at room temperature for 24 hours. After adding an aqueous solution of sodium hydrogen sulfite, the mixture was stirred for 1 hour, and insoluble substances were removed by filtration, and the filtrate was extracted with ethyl acetate. The separated organic layer was washed with water and dried, followed by removing the solvent under vaccum to obtain an oily product. It was then purified by column chromatography on a silica gel column to obtain 1.4 g of the target compound as a white solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 1 hour
  3. custominsoluble substances were removed by filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe separated organic layer was washed with water
  6. customdried
  7. customby removing the solvent under vaccum
  8. customto obtain an oily product
  9. customIt was then purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-14a12c9116a942c98a00c2b8223f9ba1
Source dataset
uspto-grants-1996_02
Patent number
US05493063

Reaction notes

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