Heptane → 1-(3-Benzyloxymethyl-2-methoxy-pyridin-4-yl)-propan-1-one

Participants

Reaction Conditions

Reaction Steps

To stirred solution of 4.120 g 3-benzyloxymethyl-4-(2-ethyl-[1,3]dioxan-2-yl)-2-methoxy-pyridine as obtained from Example 6 (12.00 mmol) in 96 mL ethanol and 24 mL water were added at room temperature 461 mg para-toluenesulfonic acid monohydrate (2.40 mmol, 0.2 eq). The mixture was subsequently heated to 80° C. and the reaction was monitored by HPLC and after 6.25 h at 80° C. (<0.2% area starting material as obtained from Example 6), the solution was cooled down to room temperature and poured into 600 mL heptane. The organic phase was washed with 600 mL water, subsequently with 600 mL aqueous NaHCO3 solution (0.1 M) and again with 600 mL water. The organic phase was dried over 20 g Na2SO4 (30 min) and filtered. The solid was washed with 40 mL heptane. After evaporation of solvent in a rotary evaporator (40° C./10 mbar), the title compound (3.302 g, 96% by weight) was obtained as a light yellow oil.

Provenance & Evidence