Example 137C Synthesis of 3-(benzyloxy)-2,2-dimethylpropan-1-ol: To a solution of 2,2-dimethylpropane-1,3-diol (2 g, 19.20 mmol) in THF (30 mL) was added 60% sodium hydride (0.256 g, 6.40 mmol) in batches and stirred for 5 minutes at room temperature. Subsequently, benzyl bromide (0.761 mL, 6.40 mmol) and tetrabutylammonium iodide (0.709 g, 1.920 mmol) were added sequentially and stirring was continued overnight at room temperature. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (150 mL) and water (50 mL) to separate the organic phase. The aqueous phase was extracted with ethyl acetate (2 x 50 mL) and the organic phases were combined. The organic phase was washed sequentially with water (2×50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 10% to 50% ethyl acetate-heptane gradient elution) to afford the target product 3-(benzyloxy)-2,2-dimethylpropan-1-ol (0.992 g, 80% yield). Product characterization data: 1H NMR (400 MHz, CDCl3) δ 7.41-7.32 (m, 5H), 4.51 (s, 2H), 3.46 (d, J=5.7 Hz, 2H), 3.33 (s, 2H), 2.55 (t, J=5.9 Hz, 1H), 0.93 (s, 6H). m/z MS (DCI+) 195.0 (M+H).
