Реакция #1121734

Уравнение реакции

linoleyl methanesulfonate

1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol

NaH

→

3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine

Выход 53.0%

Растворители

toluene

toluene

toluene

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction was then stirred for 18 hours at 90° C
2. 2
   Другоеquenched by the slow addition of ethanol (10 mL)
3. 3
   КонцентрированиеThe mixture was then concentrated
4. 4
   Экстракцияextracted three times with EtOAc (20 mL)
5. 5
   ПромывкаThe combined organic extracts were washed with deionized water (15 mL)
6. 6
   Сушкаdried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated
9. 9
   ДругоеChromatographic purification of the residue (0-5% MeOH in chloroform)

Методика

A toluene (10 mL) solution of crude 1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol (1.0 g, 4.29 mmol, 1.0 equiv) was carefully added dropwise to a toluene suspension (5 mL) of NaH (60%, 0.17 g, 4.29 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 (1.47 g, 4.29 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 then concentrated and the residue was taken up with deionized water (15 mL) and extracted three times with EtOAc (20 mL). The combined organic extracts were washed with deionized water (15 mL), dried (MgSO4), filtered, and concentrated. Chromatographic purification of the residue (0-5% MeOH in chloroform) yielded 109 mg (53% yield) of 3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine, a thick clear oil.

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