2-Cyclopropyl-6-(1,3-dioxolan-2-yl)pyridine → 6-Cyclopropylpicolinaldehyde
Reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]3OCC[O:11]3)[N:5]=2)[CH2:3][CH2:2]1>Cl.C1COCC1>[CH:1]1([C:4]2[N:5]=[C:6]([CH:10]=[O:11])[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 2-cyclopropyl-6-(1,3-dioxolan-2-yl)pyridine of Step C (538.2 mg, 2.82 mmol) in 10% aqueous HCl (5 mL) and THF (10 mL) was heated at reflux for 18 h. The cooled reaction mixture was cooled to 0° C. and quenched with saturated aqueous NaHCO3. The reaction mixture was poured into CHCl3 (20 mL). The phases were separated. The aqueous phase was extracted with CHCl3 (10 mL). The combined organic phases were dried (MgSO4), filtered and concentrated. The resulting residue was purified on a Biotage 40S column using 10% ethyl acetate in hexane as the eluent to afford 351.0 mg (2.38 mmol, 85%) of the desired aldehyde as a clear oil.