Diisobutylaluminum hydride → 5-Ethoxypyridine-3-carbaldehyde
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was quenched with 100 ml 1.0M Rochelle's salt
- extractionextracted with Et2O
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1c8fccc688e64e8796dd63804a250a36
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06268378B1
Reaction notes
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