Triacetoxyperiodinane → 3-((Tert-butyldimethylsilyl)oxy)-2,2-dimethylpropanal

HRID 1398535Notes

Reaction equation

HRID 1398535 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 590121383-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropan-1-ol

Product 1

HCID 106563753-((Tert-butyldimethylsilyl)oxy)-2,2-dimethylpropanalYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-ol (3.0 g, 13.8 mmol) in DCM (30 ml) was added Dess-Martin reagent (8.6 g, 20.6 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was then washed with water and concentrated in vacuo. The crude residue was purified by flash chromatography (eluted with petroleum ether:EtOAc=100:1) to afford the title compound (1.6 g, 54%): 1H NMR (CDCl3, 400 MHz) delta 0.05 (s, 6H), 0.88 (s, 9H), 1.17 (s, 6H), 3.59 (s, 2H).

Workup

  1. washThe reaction mixture was then washed with water
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by flash chromatography (eluted with petroleum ether:EtOAc=100:1)

Sources & evidence

ORD record
ord-14df77e9523f44cdbc49ecbb30ca8b87
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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