(3-(((Tert-butyldiphenylsilyl)oxy)methyl)phenyl)methanol → Benzaldehyde, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

HRID 1049404

Reaction equation

HRID 1049404 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH2:26][OH:27])[CH:23]=[CH:24][CH:25]=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>C1COCC1.[O-2].[Mn+4].[O-2]>[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[CH:26]=[O:27])([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:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 57049439(3-(((Tert-butyldiphenylsilyl)oxy)methyl)phenyl)methanol

Product 1

HCID 10883279Benzaldehyde, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-Yield 95.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)methanol (6.96 g) in THF (37 mL) was added manganese(IV) oxide (8.03 g), and the mixture was stirred at room temperature for 5.5 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.61 g) as a pale-yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d468fae0eea74f0eae0320f6c0260089
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Linked notes

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