Example 1: Synthesis of ethyl 2-(3-chloropropoxy)acetate (6)
3-Chloro-1-propanol (4.64 g, 0.68 mol) was dissolved in dichloromethane (0.68 L) under cooling conditions in an ice/methanol bath. To this solution, ethyl diazoacetate (5.77 g, 0.67 mol) was added, mixed thoroughly, and boron trifluoride-ether compound (1.0 g, 7.0 mmol) was added slowly. After the addition of the boron trifluoride-ether compound, the reaction started to release nitrogen. The cooling bath was removed and the reaction temperature was allowed to rise naturally to 37 °C and maintained at this temperature until the gas release stopped. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give an orange oily product. Vacuum distillation using an 8-inch high Vigreux column gave purified ethyl 2-(3-chloropropoxy)acetate (78.8 g, 65% yield).
Product characterization data: 1H-NMR (CDCl3, δ): 4.21 (q, 2H), 4.07 (s, 2H), 3.67 (m, 4H), 2.06 (p, 2H), 1.28 (t, 3H).
