反応 #1121734

反応方程式

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

収率 53.0%

溶媒

toluene

toluene

toluene

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction was then stirred for 18 hours at 90° C
2. 2
   その他quenched by the slow addition of ethanol (10 mL)
3. 3
   濃縮The mixture was then concentrated
4. 4
   抽出extracted three times with EtOAc (20 mL)
5. 5
   洗浄The combined organic extracts were washed with deionized water (15 mL)
6. 6
   乾燥dried (MgSO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他Chromatographic purification of the residue (0-5% MeOH in chloroform)

実験手順

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.

出典