2-Cyclopropyl-6-(1,3-dioxolan-2-yl)pyridine → 6-Cyclopropylpicolinaldehyde

Temperature

0 °C

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.

1. temperaturewas heated
2. temperatureat reflux for 18 h
3. customThe cooled reaction mixture
4. customquenched with saturated aqueous NaHCO3
5. additionThe reaction mixture was poured into CHCl3 (20 mL)
6. customThe phases were separated
7. extractionThe aqueous phase was extracted with CHCl3 (10 mL)
8. dry with materialThe combined organic phases were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting residue was purified on a Biotage 40S column

ORD record

ord-5b22fb7f94fa4815bb4a272b990c6103

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417041B2