Diisobutylaluminumhydride → Pyridin-3-ylacetaldehyde

HRID 1274394Notes

Reaction equation

HRID 1274394 reaction equation
CON(C)[C:4](=[O:12])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][CH:4]=[O:12])[CH:7]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 22120669N-methoxy-N-methyl-2-(pyridin-3-yl)acetamide

Product 1

HCID 11073404Pyridin-3-ylacetaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methyl-2-pyridin-3-yl-acetamide (279 mg in 5 mL dry tetrahydrofuran) at -30° C. was added 3.1 mL of a 1M diisobutylaluminum hydride solution in tetrahydrofuran and the mixture stirred at low temperature. After 30 minutes, the reaction was quenched by the careful addition of saturated aqueous sodium potassium tartarate. The resulting mixture was allowed to stir while warming to room temperature at which time the mixture was diluted with ethyl acetate and filtered through a pad of sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 94:6) gave the title compound (120 mg).

Workup

  1. customthe reaction was quenched by the careful addition of saturated aqueous sodium potassium tartarate
  2. stirringto stir
  3. additionwas diluted with ethyl acetate
  4. filtrationfiltered through a pad of sodium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol, 94:6)

Sources & evidence

ORD record
ord-5be6d44c42a349beaacf72d52d4bb910
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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