Dimethylformamide → 5-Propoxypyridine-2-carboxaldehyde
Reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH3:11])=[CH:4][N:3]=1.C1C[O:15][CH2:14]C1.C([Li])(C)(C)C.CN(C)C=O>O.C(OCC)(=O)C>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:14]=[O:15])=[N:3][CH:4]=1)[CH2:10][CH3:11]Participants
Conditions
- Temperature
- -78 °C
Procedure
A mixture comprising 2-iodo-5-propoxypyridine (0.27 g, 1 mmol) and THF (10 mL) was cooled to -78° C. and then tert-butyl lithium (1.3 mL, 1.7 M in pentane, 2.1 mmol) was added dropwise to give an orange slurry. The slurry was cooled to -78° C. and stirred for 5 minutes and then anhydrous N,N-dimethylformamide (0.4 mL, 5 mmol) was added dropwise. The mixture was allowed to warm to ambient temperature, stirred 20 minutes and then poured into a mixture comprising ethyl acetate and water. The mixture was washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to provide 5-propoxypyridine-2-carboxaldehyde (0.2 g, 1.3 mmol) as a dark oil. 1H-NMR (300 Mhz, CD3OD): 1.1 (t, 3H), 1.9 (m, 2H), 4.1 (t, 2H), 7.5 (m, 2H), 8.4 (m, 1H), 10.5 (s, 2H); MS (CI); Calculated for C9H11NO2, 165.2, Found (MH+): 166.
Workup
- customto give an orange slurry
- temperatureto warm to ambient temperature
- stirringstirred 20 minutes
- washThe mixture was washed with water
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d3d53baeb28745fcb4f6d01fe1a0a1ea
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06150379
Reaction notes
Loading…