Triacetoxyperiodinane → 1-(5-(Methoxymethoxy)-2-neopentylpyridin-4-yl)ethanone

HRID 1921959Notes

Reaction equation

HRID 1921959 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH:16]([OH:18])[CH3:17])=[CH:7][C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:9][CH:10]=1.C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:16](=[O:18])[CH3:17])=[CH:7][C:8]([CH2:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 575158751-(5-(Methoxymethoxy)-2-neopentylpyridin-4-yl)ethanol

Product 1

HCID 575158761-(5-(Methoxymethoxy)-2-neopentylpyridin-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(5-(methoxymethoxy)-2-neopentylpyridin-4-yl)ethanol (24.4 g, 96.3 mmol) and sodium bicarbonate (32.4 g, 385 mmol) in CHCl3 (500 mL) at 0° C. was added Dess-Martin Periodinane (53.1 g, 125 mmol). The reaction was stirred 5 h, quenched with saturated aqueous Na2SO3 (300 mL), extracted with CH2Cl2 (3×250 mL), the combined organic layers washed with saturated NaCl (300 mL), dried (Na2SO4), and concentrated to give a yellow oil. Purification by ISCO (330 g SiO2, 20% EtOAc/Hexane) gives 1-(5-(methoxymethoxy)-2-neopentylpyridin-4-yl)ethanone as a clear, colorless oil.

Workup

  1. customquenched with saturated aqueous Na2SO3 (300 mL)
  2. extractionextracted with CH2Cl2 (3×250 mL)
  3. washthe combined organic layers washed with saturated NaCl (300 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by ISCO (330 g SiO2, 20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-32dfddf8c1fb4beb8b7c36f8fbaa1f17
Source dataset
uspto-grants-2012_05
Patent number
US08173810B2

Reaction notes

Loading…