反应 #1121729

反应方程式

linoleyl methanesulfonate

toluene

3-(dimethylamino)-1,2-propanediol

NaH

toluene

toluene

→

1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-ol

反应条件

后处理

1. 1
   workup.STIRRINGthe reaction was then stirred for 18 hours at 90° C
2. 2
   其他quenched by the slow addition of ethanol (10 mL)
3. 3
   浓缩The mixture was concentrated
4. 4
   萃取extracted three times with EtOAc (30 mL)
5. 5
   洗涤The combined organic extracts were washed with deionized water (20 mL)
6. 6
   干燥dried (MgSO4)
7. 7
   过滤filtered
8. 8
   浓缩concentrated
9. 9
   其他Chromatographic purification of the residue (0-5% MeOH in chloroform)

实验过程

A toluene (10 mL) solution of 3-(dimethylamino)-1,2-propanediol (98%, 1.00 g, 8.39 mmol, 1.0 equiv)) was carefully added dropwise to a toluene suspension (5 mL) of NaH (60%, 0.34 g, 8.39 mmol, 1.0 equiv) at 0° C. under argon and the resultant was stirred for 15 minutes. A toluene solution (5 mL) of linoleyl methanesulfonate (2.87 g, 8.39 mmol, 1.0 equiv) was added dropwise to the stirring mixture and the reaction was then stirred for 18 hours at 90° C. The mixture was then cooled to room temperature and quenched by the slow addition of ethanol (10 mL). The mixture was concentrated and the residue was taken up with deionized water (20 mL) and extracted three times with EtOAc (30 mL). The combined organic extracts were washed with deionized water (20 mL), dried (MgSO4), filtered, and concentrated. Chromatographic purification of the residue (0-5% MeOH in chloroform) provided 1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-ol, a thick, clear oil.

来源