(2-methyl-3-phenylmethoxypropyl) methanesulfonate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (0.855 g, 6.18 mmol) and 3-(benzyloxy)-2-methylpropyl methanesulfonate (Compound 18F, 1.46 g, 5.67 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 5.2 mmol) in DMF (4 mL) and the mixture was allowed to stir at 80° C. overnight. The reaction was quenched with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was washed with water (2×30 mL), washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on a Teledyne ISCO Combiflash® Rf system using Heptane/EtOAc (70:30→30:70) as eluent to give the desired product as a light-yellow oil. 1H NMR (CDCl3, 400 MHz): δ=7.80 (s, 1H), 7.65 (s, 1H), 7.29-7.37 (m, 5H), 4.49 (s, 2H), 4.26, 4.04 (ABX, JAB=13.4 Hz, JAX=6.3 Hz, JBX=7.1 Hz, 2H), 3.32 (d, J=5.6 Hz, 2H), 2.41 (m, 1H), 1.33 (s, 12H), 0.95 (d, J=6.8 Hz, 3H). The reaction was quenched with water (20 mL) extracted with EtOAc (50 mL) The organic layer was washed with water (2×30 mL) washed with brine (30 mL) dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The residue was purified on a Teledyne ISCO Combiflash® Rf system