Diisobutylaluminum hydride → 3-Pyridinecarboxaldehyde, 5-ethoxy- (9CI)

HRID 1108411Notes

Reaction equation

HRID 1108411 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:15]=1)[C:9](N(OC)C)=[O:10])[CH3:2].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:15]=[C:8]([CH:9]=[O:10])[CH:7]=[N:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 21715825HCID 21715825, compound

Product 1

HCID 181777623-Pyridinecarboxaldehyde, 5-ethoxy- (9CI)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 16-3 (14.0 g, 66.5 mmol) and CH2Cl2 (200 mL) at -78° C. under argon was added DIBAL (1.0M hexanes, 90 ml) dropwise over 30 minutes. After 30 minutes, the solution was warmed to 0° C. for 1 hour. The reaction was quenched with 100 ml 1.0M Rochelle's salt, stirred for 1.0 hour and then extracted with Et2O. The organic layer was dried (MgSO4), and then concentrated to give the aldehyde 16-4 as a brown oil.

Workup

  1. customThe reaction was quenched with 100 ml 1.0M Rochelle's salt
  2. extractionextracted with Et2O
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0d5bb1b1f61a4a458a15e8e99ffe20ef
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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