2-t-Butyldimethylsilyloxymethyl-6-hydroxymethylnaphthalene → 2-t-Butyldimethylsilyloxylmethylnaphthalene-6-carboxaldehyde

HRID 348733Notes

Reaction equation

HRID 348733 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:20][OH:21])[CH:16]=2)[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:20]=[O:21])[CH:16]=2)[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 230792982-t-Butyldimethylsilyloxymethyl-6-hydroxymethylnaphthalene

Product 1

HCID 230793282-t-Butyldimethylsilyloxylmethylnaphthalene-6-carboxaldehydeYield 96.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

The compound (255 mg) obtained in Example 121-2 was dissolved in chloroform (5.0 ml) and then added with manganese dioxide (chemically processed product) (366 mg), followed by stirring overnight at room temperature. After completion of the reaction, the solution was filtrated through Celite and the solvent was then distilled off, thereby obtaining the subject compound (245 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe solution was filtrated through Celite
  3. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-3c8407cb9a60447980da25cca394a72f
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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