Triacetoxyperiodinane → 5-(4-Chloro-benzyloxy)-4-methoxy-pyridine-2-carbaldehyde

HRID 1261108Notes

Reaction equation

HRID 1261108 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[C:9]([O:16][CH3:17])=[CH:10][C:11]([CH2:14][OH:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[C:9]([O:16][CH3:17])=[CH:10][C:11]([CH:14]=[O:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58087092[5-(4-Chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-methanol

Product 1

HCID 580874295-(4-Chloro-benzyloxy)-4-methoxy-pyridine-2-carbaldehydeYield 72.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[5-(4-Chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-methanol (640, 480 mg, 1.7 mmol) was dissolved in dimethyl sulfoxide (26 mL) and Dess-Martin periodinane (909 mg, 2.1 mmol) was added. The reaction was allowed to stir at room temperature for 2 hours. The reaction was concentrated under high vacuum and then poured into a solution of NaHCO3 and Na2S2O3. The mixture was extracted with ethyl acetate. The organic portions were dried with anhydrous sodium sulfate and filtered. The filtrate was adsorbed onto silica and purified by silica gel chromatography, ethyl acetate:hexanes, to provide the desired compound as a white powder (641, 343 mg, 72%).

Workup

  1. concentrationThe reaction was concentrated under high vacuum
  2. additionpoured into a solution of NaHCO3 and Na2S2O3
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic portions were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. custompurified by silica gel chromatography, ethyl acetate

Sources & evidence

ORD record
ord-d6be2bef255c4de799aebb367caec86b
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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