Water → 6-Methoxypyridine-3-carbaldehyde

HRID 1663001Notes

Reaction equation

HRID 1663001 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][N:4]=1.C(N(CC)CC)C.O>CS(C)=O>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([CH:9]=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 12259941(6-Methoxypyridin-3-yl)methanol

Product 1

HCID 33645766-Methoxypyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

10 g (71.9 mMol) of 2-methoxy-5-hydroxymethylpyridine (preparation see Heterocycl. Commun. 1999, 5, 257) are dissolved in 160 ml of DMSO and 30 ml (215 mMol) of triethylamine. At RT (exothermic-cool!), 34.3 g (215 mMol) of sulfur trioxide pyridine complex in 160 ml DMSO are added dropwise, and the mixture is stirred 1 h at RT. The mixture is poured into water and extracted three times with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and evaporated to yield the title compound: HPLC(Grad5-40) tRet=12.9.

Workup

  1. additionare added dropwise
  2. extractionextracted three times with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-675619f6a206450ea9818bdc3ab9f569
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

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