6-Methyl-2-pyridinecarboxaldehyde → HCID 54342320, compound

HRID 1720371Notes

Reaction equation

HRID 1720371 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CC.C[C:30]1[N:35]=[C:34]([CH:36]=O)[CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH:1]([C:30]1[N:35]=[C:34]([CH3:36])[CH:33]=[CH:32][CH:31]=1)=[CH:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 80374Propyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 54342320HCID 54342320, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

n-Butyllithium (7.5 mL, 1.6M/hexanes, 12 mmol) was added to a slurry of propyltriphenylphosphonium bromide (4.62 g, 12 mmol) in THF (40 mL) at -78° C. The mixture was warmed to 0° C. and stirred 30 min., then cooled again to -78° C. A THF (10 mL) solution of 6-methyl-2-pyridinecarboxaldehyde (1.21 g, 10 mmol) was added dropwise. The reaction mixture was allowed to warm to r.t. and stirred for 2 hours. Silica gel was added and the slurry was filtered on a short (SiO2) column eluting with 10% EtOAc in hexanes to give 990 mg of the title compound.

Workup

  1. temperaturecooled again to -78° C
  2. temperatureto warm to r.t.
  3. stirringstirred for 2 hours
  4. additionSilica gel was added
  5. filtrationthe slurry was filtered on a short (SiO2) column
  6. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-a0f683efd7ad42a3a2731ef7d387c96e
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

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