Sodium Thiosulfate → 1-(3-(Methoxymethoxy)pyridin-4-yl)ethanone

HRID 552801Notes

Reaction equation

HRID 552801 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[CH:33]([OH:35])[CH3:34].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:33](=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 575158511-(3-(Methoxymethoxy)pyridin-4-yl)ethanol

Product 1

HCID 575158521-(3-(Methoxymethoxy)pyridin-4-yl)ethanoneYield 86.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dess-Martin periodinane (18 g, 43 mmol) was added to a stirring mixture of 1-(3-(methoxymethoxy)pyridin-4-yl)ethanol (4.6 g, 25 mmol), NaHCO3 (6.3 g, 75 mmol), and CHCl3 (75 mL) at RT. After 24 h, 1.0 M aqueous Na2S2O3 was added, the reaction mixture was stirred for 90 min, partitioned between ethyl acetate and 1.0 M aqueous Na2S2O3, the layers were separated, the organic material was washed with 1.0 M aqueous Na2S2O3, water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (gradient elution; 2:1→1:1 hexane-ethyl acetate) to give 3.9 g (86%) of 1-(3-(methoxymethoxy)pyridin-4-yl)ethanone as a clear yellow-orange oil.

Workup

  1. custompartitioned between ethyl acetate and 1.0 M aqueous Na2S2O3
  2. customthe layers were separated
  3. washthe organic material was washed with 1.0 M aqueous Na2S2O3, water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash chromatography on silica gel (gradient elution; 2:1→1:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-eecf1a3d96e84c0bb6385c4d9fc90339
Source dataset
uspto-grants-2011_05
Patent number
US07951838B2

Reaction notes

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