[Synthesis]
A solution of triphenylphosphine (2.42 g, 9.25 mmol) and imidazole (1.26 g, 18.49 mmol) in dichloromethane (20 mL) was added to a round-bottomed flask and cooled to 0°C in an ice bath. To this cooled solution was added iodine (2.35 g, 9.25 mmol). After the iodine was completely dissolved, a solution of (3,3-dimethoxycyclobutyl) methanol (1.04 g, 7.11 mmol) in dichloromethane (10 mL) was added. The reaction mixture was stirred at 0°C for 30 minutes, followed by continued stirring at 25°C for 2 hours. Upon completion of the reaction, the reaction was poured into ice-cold water (50 mL) and extracted with dichloromethane (2 × 30 mL). The organic layers were combined, washed with 1.0 N sodium thiosulfate solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by fast column chromatography (Merck silica gel 60, 230-400 mesh, elution gradient: 30% ethyl acetate/hexanes to 40% ethyl acetate/hexanes) afforded 3-(iodomethyl)-1,1-dimethoxycyclobutane (1.34 g, 74% yield) as a light yellow oil.1H NMR (300 MHz, CDCl3) δ ppm: 1.72- 1.81 (m, 2H, CH2), 2.28-2.53 (m, 3H, CH2 and CH), 3.14 (s, 3H, OCH3), 3.16 (s, 3H, OCH3), 3.29 (d, J = 7.7 Hz, 2H, ICH2). |