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

Participants

Reaction Steps

To a solution of ZnCl2 in THF (0.5 M, 25 mL) was added dropwise a solution of cyclopropylmagnesium bromide (0.5 M, 25 mL) at −78° C. under nitrogen. The reaction mixture was then allowed to warm up to room temperature and stirred for an hour. The above mixture was then transferred to a sealed tube with 2-bromo-6-[1,3]dioxolan-2-yl-pyridine (1.9 g, 8.25 mmole, see subpart (a) above) and Pd(PPh3)4 (0.4 g, 0.35 mmole). TLC showed major formation of the product and some starting material. The mixture was then heated to 120° C. for 2 hours and cooled down to room temperature and then worked up with EtOAc and saturated ammonium chloride and dried over MgSO4. The residue from concentration was purified on silica gel column with 5% EtOAc in CH2Cl2 to yield 2-cyclopropyl-6-[1,3]dioxolan-2-yl-pyridine as a bright yellow liquid (0.96 g, 61%).

Provenance & Evidence