Hydrogen Peroxide → HCID 66785983, compound

HRID 1615082Notes

Reaction equation

HRID 1615082 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:29]O.O>C(Cl)(Cl)Cl.C[Re](=O)(=O)=O.[O-2].[O-2].[Mn+4]>[Si:22]([O:21][CH2:20][CH:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N+:17]([O-:29])=[CH:16][CH:15]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24]

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 66786291HCID 66786291, compound2×

Product 1

HCID 66785983HCID 66785983, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 178477782HCID 178477782, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 4-[5-(tert-butyldimethylsilanyloxy)-4-(tert-butyldimethylsilanyloxymethyl)-pentyl]pyridine (0.43 g) prepared in (4) in chloroform (5.0 mL) were added methyltrioxorhenium (VII) (0.0030 g) and aqueous 30% hydrogen peroxide (0.21 mL). The reaction mixture was stirred at RT for 4 hr. An appropriate amount of manganese dioxide (IV) was added to the reaction mixture. The mixture was stirred for 1 hr. Water was added to the mixture and the mixture was extracted with chloroform. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure to obtain the crude title compound.

Workup

  1. stirringThe mixture was stirred for 1 hr
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-214c056a13994fef8645efd3c44c0e63
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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