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8. Representative procedure: To a stirred solution of 2-phenyloxirane 5 (1 g,
8.31 mmol) in anhydrous tetrahydrofuran was added sodium bis(trimethylsilyl)
amide (1 M solution in THF, 29.08 mL, 29.08 mmol, 3.0 equiv) at 0–5 °C. The
resultant mixture was allowed to warm to 25 °C and stirred for 20 h, by which
time the reaction was completed as indicated by TLC. The reaction mixture was
then quenched with water (2.5 mL) and stirred for 5 h. The solvent was removed
by distillation under reduced pressure bringing the total volume to one-fourth.
The content of the reaction mixture was extracted with dichloromethane
(2 Â 10 mL). The organic layer was dried over anhydrous Na
2 4
SO and
concentrated under reduced pressure to give the crude product. The crude
product was purified by column chromatography on silica gel to obtain the pure
product as pale yellow solid.