MAGNESIUM SILICATE (synthetic) → HCID 21706141, compound

HRID 650917Notes

Reaction equation

HRID 650917 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[C:14]3[C:9](=[CH:10][C:11]([CH2:16][OH:17])=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1.[O-][Si]([O-])=O.[Mg+2]>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][O:2][C:3]1[C:15]2[C:14]3[C:9](=[CH:10][C:11]([CH:16]=[O:17])=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 21706137HCID 21706137, compound

Product 1

HCID 21706141HCID 21706141, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 1.85 g (7.69 mmol) of carbinol from Step E in 50 mL CH2Cl2 was added 270.1 mg (0.769 mmol) of tetrapropylammonium perruthenate. After stirring for 5 minutes, 1.35 g (11.5 mmol) of solid N-methyl-morpholine-N-oxide was added all at once, and the resulting mixture stirred further for 5 minutes. The dark solution was passed over a column of florisil eluted with CH2Cl2-EtOAc (10:1) to give 1.42 g of the title aldehyde as a yellow solid.

Workup

  1. stirringstirred further for 5 minutes
  2. washeluted with CH2Cl2-EtOAc (10:1)

Sources & evidence

ORD record
ord-68bd16189b484e7c907d07083a2faa51
Source dataset
uspto-grants-2001_08
Patent number
US06277843B1

Reaction notes

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