反应详情

To a stirred solution of the diol (344) (12.7 g, 58.5 mmol) and triethylamine (5 equiv., 41 mL) in CH2Cl2 (200 mL) at 0° C. was added methanesulfonyl chloride (NsCl) (2.4 equiv., 10.9 mL). The resulting suspension was removed from the ice bath and allowed to warm to room temperature with stirring at which point TLC analysis indicated complete consumption of the starting material and conversion to a single spot of higher Rf (5% MeOH/CHCl3, stained with K2MnO4). The reaction was quenched by the addition of water (20 mL) with vigorous stirring. NaHCO3 (sat., aqueous, 200 mL) was added and the organic layer was separated, washed with brine, dried (MgSO4) and purified by flash chromatography (1–10% MeOH/CHCl3) to yield the desired compound (345) as a colorless oil.

1. customThe resulting suspension was removed from the ice bath
2. customconsumption of the starting material and conversion to a single spot of higher Rf (5% MeOH/CHCl3, stained with K2MnO4)
3. customThe reaction was quenched by the addition of water (20 mL) with vigorous stirring
4. additionNaHCO3 (sat., aqueous, 200 mL) was added
5. customthe organic layer was separated
6. washwashed with brine
7. dry with materialdried (MgSO4)
8. custompurified by flash chromatography (1–10% MeOH/CHCl3)