Triacetoxyperiodinane → 8-(Tert-butyl-dimethyl-silanyloxymethyl)-naphthalene-1-carbaldehyde

HRID 1793580Notes

Reaction equation

HRID 1793580 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:21])([CH3:20])[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([CH2:18][OH:19])=[CH:15][CH:14]=[CH:13]2)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[C:1]([SiH2:5][O:6][C:7]([CH3:21])([CH3:20])[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([CH:18]=[O:19])=[CH:15][CH:14]=[CH:13]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 137328532[8-(tert-Butyl-dimethyl-silanyloxymethyl)-naphthalen-1-yl]-methanol

Product 1

HCID 1373285318-(Tert-butyl-dimethyl-silanyloxymethyl)-naphthalene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[8-(tert-Butyl-dimethyl-silanyloxymethyl)-naphthalen-1-yl]-methanol (Aust. J. Chem. 1996, 49, 793–800) (0.2 g, 0.66 mmol) was dissolved in dichloromethane (8 mL). To the solution was then added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H)-one, also known as Dess-Martin periodinane (0.56 g, 1.32 mmol). The reaction mixture was stirred for 1 hr then partitioned with an aqueous saturated solution of thiosulfate and dichloromethane. The organic layer was washed with an aqueous saturated solution of thiosulfate, an aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (6.0% ammonia 2.0 M in methanol/dichloromethane) to yield 8-(tert-butyl-dimethyl-silanyloxymethyl)-naphthalene-1-carbaldehyde as a clear oil.

Workup

  1. customthen partitioned with an aqueous saturated solution of thiosulfate and dichloromethane
  2. washThe organic layer was washed with an aqueous saturated solution of thiosulfate
  3. dry with materialan aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude oil
  7. customThe crude oil was purified via flash chromatography (6.0% ammonia 2.0 M in methanol/dichloromethane)

Sources & evidence

ORD record
ord-72af2a30687844fa9df2bfb9b8bbf530
Source dataset
uspto-grants-2006_07
Patent number
US07081463B2

Reaction notes

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