General procedure for the synthesis of (3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate from 3-methyl-3-hydroxymethoxetane and p-toluenesulfonyl chloride:
Step 1: To a solution of (3-methyloxetan-3-yl)methanol (1 g, 9.79 mmol) in dichloromethane (15 ml) was added triethylamine (2.71 ml, 19.58 mmol) followed by p-toluenesulphonyl chloride (1.867 g, 9.79 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 3 to 5 hours. Upon completion of the reaction, the reaction mixture was quenched with water, the organic layer was extracted with ethyl acetate and purified by column chromatography to afford the title compound (3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (1.875 g) as a white solid in 74.7% yield.
Product characterization data: 1H NMR (DMSO-d6, 300 MHz): δ 7.82 (d, J = 8.1 Hz, 2H), 7.51 (d, J = 8.1 Hz, 2H), 4.25 (d, J = 5.7 Hz, 2H), 4.19 (d, J = 6.0 Hz, 2H), 4.11 (s, 2H), 2.43 (s, 3H), 1.18 (s, 3H); MS (ESI): m/z 279.0 (M + Na).
