Chlorotrimethylsilane → (2RS,3SR)-3-(2-Ethoxyphenoxy)-2-hydroxy-3-phenyl-1-(trimethylsilyloxy)propane

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Reaction Conditions

Reaction Steps

3-(2-Ethoxyphenoxy)-2-hydroxy-3-phenylpropanol from Example 2 (1.44 g, 5 mmole) and triethylamine ((0.77 mL, 5.5 mmole) were dissolved in ethyl acetate (15 ml) and cooled to −17° C. Trimethylsilyl chloride (0.64 mL, 5.0 mmole) dissolved in 5 mL of ethyl acetate was added over 10 minutes keeping the temperature below −15° C. a white precipitate formed during this addition. The mixture was stirred below −15° C. for 15 minutes, and 20 mL of pentane was added. The solids were removed by filtration and the filtrate was concentrated under vacuum to a cloudy oil. The oil was chromatographed on silica (230-400 mesh) eluting with 4:1 heptane-ethyl acetate. The product-containing fractions were concentrated to yield 1.80 g (88.5%) of the title compound as a clear colorless oil; 1H NMR (400.13 MHZ, CDCl3) d 0.09 (s, 9H), 1.47 (t, J=6.8 Hz, 3H), 2.82 (d, J=5.2, 1H), 3.80 (m, 3H), 4.0-4.11 (m, 4H), 5.08 (d, J=6.0, 1H), 6.76 (m, 2H), 6.85 (m, 2H), 7.2-7.45 (m, 5H); 13C NMR (100.62 MHZ, CDCl3) d 0.0, 15.54, 63.34, 65.06, 75.22, 83.71, 114.28, 118.60, 121.51, 122.95, 127.84, 128.49, 128.84, 138.93, 148.34, 150.40; MS (ei) m/e 360.

Provenance & Evidence