Triacetoxyperiodinane → 2-(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)acetaldehyde

HRID 41150Notes

Reaction equation

HRID 41150 reaction equation
[CH:1]([Si:4]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[O:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=1)([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH:17]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:20]([CH3:22])[CH3:21])[O:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH2:14][CH:15]=[O:16])[CH:11]=[CH:12][CH:13]=1)([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 547578682-(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)ethanol

Product 1

HCID 547579592-(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)acetaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 53 (0.170 g, 0.527 mmol) in dichloromethane (4 mL) was added with Dess-Martin periodinane (0.270 g, 0.632 mmol) and stirring was maintained for 4 h at rt. The reaction mixture was filtered through a pad of celite and then concentrated to dryness. The residue so obtained was purified by silica gel column chromatography, using gradients of ethyl acetate in hexanes as eluent, to obtain the desired compound. Yield 77%.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated to dryness
  3. customThe residue so obtained
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-639214b9af314a12a1f8b66d531df996
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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