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

HRID 1173986Notes

Reaction equation

HRID 1173986 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-739d8e73017d4d59bcfe39f34cea6991
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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