[5-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]methanol → 5-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carbaldehyde

HRID 1881932Notes

Reaction equation

HRID 1881932 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([CH2:25][OH:26])=[N:22][N:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([CH:25]=[O:26])=[N:22][N:21]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 59331609[5-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]methanol

Product 1

HCID 593316265-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carbaldehydeYield 71%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of [5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]methanol (242 mg) in toluene (2 mL) was added manganese dioxide (693 mg), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated to give the title compound (171 mg) as a colorless amorphous solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-20ad57e2cdbe488098195c30815b7055
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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