반응 #1121737

반응 방정식

linoleyl methanesulfonate

toluene

3-(dimethylamino)-1,2-propanediol

NaH

toluene

toluene

→

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

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction was then stirred for 18 hours at 90° C
2. 2
   기타quenched by the slow addition of ethanol (10 mL)
3. 3
   농축The mixture was concentrated
4. 4
   추출extracted three times with EtOAc (30 mL)
5. 5
   세척The combined organic extracts were washed with deionized water (20 mL)
6. 6
   건조dried (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타Chromatographic purification of the residue (0-5% MeOH in chloroform)

실험 절차

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.

출처