Triacetoxyperiodinane → 2-Fluoroisonicotinaldehyde

HRID 1256612Notes

Reaction equation

HRID 1256612 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 11332468(2-Fluoropyridin-4-yl)methanol

Product 1

HCID 27629902-FluoroisonicotinaldehydeYield 30.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.64 g of 2-fluoro-4-pyridinemethanol, 10 ml of chloroform and 2.54 g of Dess-Martin Periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) was stirred for 30 minutes at room temperature. A saturated sodium hydrogen carbonate aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.19 g of 2-fluoropyridine-4-carbaldehyde.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f1d5d5e012546e3b72beb33cf9c91ca
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

Loading…