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MEM protection was also achieved using CH2Cl2 as the solvent and in a sealed tube. The purity of this reaction was slightly superior, though the yields were lower. The alternate procedure is as follows: To a stirring solution of 10 (280 mg, 0.55 mmol) in a sealed tube in CH2Cl2 (17 mL) at -30°C under N2 were added (i-Pr2)NEt (0.87 mL, 5.0 mmol) and then MEM-Cl (0.38 mL, 3.3 mmol, The reaction mixture was allowed to warm to room temperature, and the system was closed and heated at 80°C for 18 h. The mixture was then cooled, and saturated aqueous NaHCO3 (20 mL) was added. The aqueous layer was extracted with CH2Cl2 (2 x 20 mL, and the combined organic extracts were washed with brine (20 mL, dried (Na2SO 4, and concentrated. Flash chromatography (4:1 hexanes/ EtOAc) gave 12 145 mg, 44, as a clear oil
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