Dimethylformamide → 5-(Dimethoxymethyl)picolinaldehyde

HRID 885837Notes

Reaction equation

HRID 885837 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:16][CH3:17])[O:14][CH3:15])=[CH:9][N:8]=1.CN([CH:21]=[O:22])C>CCCCCC.C1COCC1.O>[CH3:15][O:14][CH:13]([O:16][CH3:17])[C:10]1[CH:11]=[CH:12][C:7]([CH:21]=[O:22])=[N:8][CH:9]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 64252132-Bromo-5-(dimethoxymethyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 184267805-(Dimethoxymethyl)picolinaldehydeYield 53.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 2.5 M BuLi in hexane (7.6 ml) was added drop-wise, under a N2 atmosphere, to a solution of 2-bromo-5-dimethoxymethyl-pyridine (3.66 g, 15.84 mmol) in THF (60 ml) at −70° C. After 15 minutes, DMF (1.82 ml, 23.5 mmol) was added drop-wise and the mixture was stirred for 30 minutes at −70° C. and then allowed to reach room temperature. The reaction was diluted with H2O and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated to dryness in vacuo. The crude product was purified by flash chromatography (petroleum ether: AcOEt 7:3) to obtain 1.54 g of 5-dimethoxymethyl-pyridine-2-carbaldehyde as a yellow oil.

Workup

  1. customat −70° C
  2. customto reach room temperature
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customThe crude product was purified by flash chromatography (petroleum ether: AcOEt 7:3)

Sources & evidence

ORD record
ord-dfebf1fb641e4b699ce82772e6849100
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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