Triacetoxyperiodinane → 2,6-Dichloropyridine-3-carbaldehyde

HRID 1399877Notes

Reaction equation

HRID 1399877 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:10])[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 12259932(2,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 122593832,6-Dichloropyridine-3-carbaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,6-dichloropyridin-3-yl)methanol (1.0 g, 5.62 mmol) in CH2Cl2 (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26° C. After addition the mixture was stirred at room temperature for 2 h. Once the reaction was complete, the mixture was then quenched by adding 5% aqueous Na2S2O3 and stirred for 30 min. The resulting mixture was extracted with CH2Cl2 (2×30 ml). The combined organic layers were washed with saturated Na2S2O3 solution (50 ml), brine (30 ml), dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification. (800 mg, Yield 80%). 1H NMR (400 MHz, CDCl3): 10.38 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H).

Workup

  1. additionAfter addition the mixture
  2. customthe mixture was then quenched
  3. additionby adding 5% aqueous Na2S2O3
  4. stirringstirred for 30 min
  5. extractionThe resulting mixture was extracted with CH2Cl2 (2×30 ml)
  6. washThe combined organic layers were washed with saturated Na2S2O3 solution (50 ml), brine (30 ml)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-109fde2cc7c445c584071d1024aca34a
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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