[6-[Tert-butylsilyloxy(diphenyl)methyl]-2-pyridinyl]methanol → 6-[Tert-butylsilyloxy(diphenyl)methyl]pyridine-2-carbaldehyde

HRID 744178Notes

Reaction equation

HRID 744178 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([O:16][SiH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:8]2[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[C:22]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([O:16][SiH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:8]2[N:13]=[C:12]([CH:14]=[O:15])[CH:11]=[CH:10][CH:9]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 131719561[6-[Tert-butylsilyloxy(diphenyl)methyl]-2-pyridinyl]methanol

Product 1

HCID 1317195606-[Tert-butylsilyloxy(diphenyl)methyl]pyridine-2-carbaldehydeYield 95.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

100 g of manganese dioxide is added in portions to a solution of 20 g of 6-(diphenyl-tert-butylsilyloxymethyl)-2-hydroxymethylpyridine in 236 ml of toluene at 24° C. under nitrogen and stirred for 24 hours. It is filtered on Celite, rewashed well with toluene and concentrated by evaporation in a vacuum. 19.0 g of the title compound is obtained as colored liquid, which is further used without further purification.

Workup

  1. filtrationIt is filtered on Celite
  2. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-475f402569424aaebb42213f9837a06b
Source dataset
uspto-grants-1996_09
Patent number
US05559134

Reaction notes

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