Triacetoxyperiodinane → 1-(6-Methoxy-2-methyl-3-pyridinyl)-1-propanone

HRID 1671324Notes

Reaction equation

HRID 1671324 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([CH:10]([OH:13])[CH2:11][CH3:12])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67336369HCID 67336369, compound

Product 1

HCID 673358811-(6-Methoxy-2-methyl-3-pyridinyl)-1-propanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(6-methoxy-2-methyl-pyridin-3-yl)-propan-1-ol (1.15 g, 6.35 mmol) in DCM (20 ml) is treated with Dess-Martin periodinane (2.96 g, 6.98 mmol) and the resulting suspension stirred at RT overnight. The reaction mixture is diluted with DCM (80 ml) and sat NaHCO3 (50 ml) added. The organic layer is separated and washed with H2O (20 ml), brine (20 ml), dried (MgSO4) and concentrated in vacuo. The resulting residue is purified by chromatography on silica gel (2×70 ml) using 50% EtOAc/iso-hexane to give 1-(6-methoxy-2-methyl-pyridin-3-yl)-propan-1-one as a white solid. MS: m/z 180.2 [M+H]+.

Workup

  1. additionadded
  2. customThe organic layer is separated
  3. washwashed with H2O (20 ml), brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified by chromatography on silica gel (2×70 ml)

Sources & evidence

ORD record
ord-e977fea0ae304aa68bbb129b9bab52c0
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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