1,3-Propanediol → 5-Bromo-2-(1,3-dioxan-2-yl)pyridine

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Reaction Steps

To solution of 5-bromo-2-formylpyridine (10 g, 53.8 mmol), 1,3-propanediol (3.89 mL, 53.8 mmol) in toluene (30 mL) was added CSA (1.249 g, 5.38 mmol). The reaction mixture was heated to reflux for 4 h with a Dean-Stark trap. The reaction mixture was quenched by addition of saturated solution of sodium bicarbonate and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford compound 278 (13.37 g, 54.8 mmol, 101% yield, crude) as a brown solid that was used in the next step with no additional purification. MS (m/z): 244.06-246.06 (M+H).

Provenance & Evidence