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

HRID 729776Notes

Reaction equation

HRID 729776 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-f8d5453d49a64d47aff283c5fce0dc7d
Source dataset
uspto-grants-2009_09
Patent number
US07582649B2

Reaction notes

Loading…