4-[(2,3-Epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolane

106-89-8

100-79-8

1607-37-0

1-Chloro-2,3-epoxypropane (198 mmol) was mixed with 2,2-dimethyl-1,3-dioxolane-4-methanol (98 mmol) in benzene (20 mL) and 50% aqueous NaOH (20 mL), and tetra-n-butylammonium bromide (TBAB, 10 mmol) was added as a phase transfer catalyst. The reaction mixture was stirred at 0 °C for 48 hours. After completion of the reaction, the reaction mixture was diluted with ether and washed sequentially with water (3 × 75 mL), saturated NaHCO3 solution (3 × 75 mL) and brine (3 × 75 mL). The organic phase was dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by reduced pressure distillation (165 °C, 1.2 mbar, boiling point 90 °C) to give 4-[(2,3-epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolane (3b) as a colorless liquid in 29% yield.1H NMR (500 MHz, CDCl3): δ 1.34 (s, 3H, CH3), 1.40 (s, 3H, CH3), 2.58 (ddd, J = 5.0, 3.9, 2.7 Hz, 1H, H-7), 2.73-2.82 (m, 1H, H-7), 3.08-3.18 (m, 1H), 3.40 (ddd, J = 17.6, 11.7, 6.0 Hz, 1H), 3.46-3.64 (m, 2H), 3.71 (td, J = 8.3, 6.4 Hz, 1H), 3.80 (ddd, J = 13.4, 11.7, 2.9 Hz, 1H), 4.04 (ddd, J = 8.0, 6.4, 1.5 Hz, 1H), 4.27 (dq, J = 11.6, 5.8, 5.3 Hz, 1H, H-1) ppm.1H NMR data are in agreement with the literature reports.