Sodium Sulfate → (4-((Triisopropylsilyl)oxy)phenyl)methanol

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Reaction Conditions

Reaction Steps

To 75 mL of dry diethyl ether was added a solution of lithium aluminium hydride (4M in diethyl ether, 14 mL, 55.8 mmol), and the solution was cooled to 0° C. A solution of ethyl 4-{[tris(1-methylethyl)silyl]oxy}benzoate (Step 1, 9.0 g, 27.9 mmol) in dry diethyl ether (90 mL) was added dropwise, maintaining the temperature below 5-10° C. After the addition was completed, stirring of the reaction mixture was continued for 1 h at 0° C. Then, still at the same temperature, a saturated aqueous solution of sodium sulfate (60 mL) was added with caution. After warming to rt, the precipitate which had formed was removed by filtration, and the residue was washed with diethyl ether. The organic layer was separated from the filtrate, and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo. The crude product thus obtained was purified by MPLC (silica, cyclohexane/ethyl acetate 5:1→1:1) to afford the title compound in pure form (7.38 g, 94%): 1H NMR (400 MHz, CDCl3) δ 7.21 (d, 2H), 6.87 (d, 2H), 4.60 (d, 2H), 1.56 (t, 1H), 1.23 (m, 1H), 1.10 (d, 18H); EI-MS m/z 280 (M)+; HPLC RT (Method H) 5.33 min.

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