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温度

0 °C

To a cooled solution of 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzyl alcohol 14 (9.5 g, 35.4 mmol) in benzene (50 mL) under nitrogen, thionyl chloride (6.32 g or 3.87 mL, 53.1 mmol) dissolved in benzene (5 mL) was added over 10 min and maintained the temperature at 0° C. for 2 h. The completion of reaction was checked by TLC (chloroform on silica gel plate). Ice was added to the reaction mixture and the solution was extracted with ethylacetate. The organic layer was washed with saturated bicarbonate solution and water and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo afforded 15. Yield: 98.5%; yellow oil. 1H NMR: δ 0.16 (s, 6H, 2×CH3), 1.00 (s, 9H, 3×CH3), 3.80 (s, 3H, OCH3), 4.44 (s, 2H, CH2), 6.70-7.01 (m, 3H, Ar—H). Anal. Calcd for C14H23ClO2Si: C, 58.62, H, 8.08. Found: C, 58.69, H, 8.03.

1. additionwas added over 10 min
2. customThe completion of reaction
3. additionIce was added to the reaction mixture
4. extractionthe solution was extracted with ethylacetate
5. washThe organic layer was washed with saturated bicarbonate solution and water
6. dry with materialdried over anhydrous sodium sulfate
7. customRemoval of the solvent in vacuo