有关三苯基氧化磷的反应:
铜盐:
1) 用 rxn(rxn is short for reaction) w/ sat NH4Cl aq
solution淬灭反应,室温搅拌几个小时直至溶液变为深蓝色。
2) 移除水相,用NH4Cl水溶液洗几次
3) 再处理粗产物
硼类化合物:许多硼类化合物及其残留物( hydroboration, allylation,
reduction, Suzuki coupling,
etc硼氢化反应、烯丙基化反应、还原反应、Suzuki偶合反应)可以通过不断重复在甲醇中浓缩溶液进行移除,在该过程中生成
R3Sn-X 副产物:
1. 锡碱反应的副产物,如Bu3SnBr可以通过用 AlMe3
处理来移除,该过程将无极性的Bu3SnMe和氢氧化钠生成极性的 Bu3SnOH(See:
P. Renaud, E. Lacote, L. Quaranta
2.
3.
a) 用合适的溶剂稀释反应混合物。
b) 加入水相 (water, sat. NH4Cl, etc.)
c) 移除水相,用1M KF aq
solution洗涤有机相2-3次。每次洗涤须在分液漏斗中摇晃1分钟左右。固体的
d) 用aq 1 X brine(盐水)洗涤,干燥有机相移除反应溶剂。
4. 在许多Stille 反应中,Bu3SnX 可以通过硅胶(2-5%三乙胺在洗脱剂中 )过滤或者直接过柱子除去。
要比用KF溶液洗涤的方法更快,且more fun than grinding a big bowl of toxic KF with silica or celite for a good dispersion. (contributed by )
5. 对于Bu3SnH而言:加入碘,将 Bu3SnSnBu3和未转换的Bu3SnH转化为Bu3SnI, KF处理(如上),将其转化为Bu3SnF,更容易移除。 (contributed by )
金属盐
许多过渡金属可以通过过滤其硫化物的方法出去。用硫化钠溶液洗涤,如果需要的化调节pH生成H2S。一些过渡金属盐可以通过
与三羟甲基磷水溶液萃取的方法出去。(See: R. H. Grubs Tetrahedron
铝盐基反应: (from the Merlic Group at UCLA, )
A. x g氢化铝锂的反应
- 乙醚稀释冷却至 0oC
- 缓慢加入 x mL
水 - 加入
x mL 15 % 氢氧化钠水溶液 - 加入 3x mL
水 - 加热至室温搅拌15 min
- 加入一些无水硫酸镁
- 搅拌15min过滤除去盐类
B. 处理含有x mmol
- 乙醚稀释冷却至 0oC
- 缓慢加入 0.04x mL
水 - 加入
0.04x mL 15 % 氢氧化钠水溶液 - 加入 0.1x mL
水 - 加热至室温搅拌15 min
- 加入一些无水硫酸镁
- 搅拌15min过滤除去盐类
钛: 用氯化铵水溶液淬灭反应, 钛副产物会留在水相中。
铬氧化物:
1. PCC/PDC: through a pad of florisil(硫酸镁)载体过滤反应混合物.
2. Jones: 加入异丙醇,直至反应从黄色/红色转变为绿色:这说明所有的氧化物被消耗完了。
m-CPBA:
If reaction is done in refluxing DCE (for example), cool reaction mixture to 0oC to precipitate out all m-CPBA. Then add 10% aqueous solution of Na2SO4. Two layers form. Separate and extract with DCM. Repeat the addition of Na2SO4 several times then combine all organic layers, wash with saturated solution of NaHCO3, then saturated aqueous solution of NaCl, then dry (MgSO4) and evaporate under reduced pressure. If purifying product by FCC, any m-CPBA still present is easily separated as it is UV active, extremely polar and it ends to deposit on column tip during purification. This is easily taken care of as m-CPBA is soluable in EtOAc.
DCC:
Filter the reaction mixture through a medium frit, rinsing with a minimal amount of reaction solvent, then work up. Depending one runs reaction in dioxane, THF, DMF, dichloromethane, etc., but urea is mostly insoluble in most solvents and this is a good way to get rid of it (the rest can be flashed away pretty straightforwardly). If it is too soluble, one can concentrate the reaction mixture first and take it up in ether, then filter and rinse. (contributed by )
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