Реакция #1121728

Уравнение реакции

Succinic anhydride

3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol

→

4-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураthe resultant was refluxed for 18 hours under argon
2. 2
   КонцентрированиеThe mixture was concentrated
3. 3
   workup.DISSOLUTIONdissolved in EtOAc (10 mL)
4. 4
   workup.ADDITIONpoured into deionized water (20 mL)
5. 5
   ДругоеThe layers were separated
6. 6
   Экстракцияthe aqueous layer was extracted with two additional portions of EtOAc (25 mL)
7. 7
   СушкаThe combined organic extracts were dried (MgSO4)
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated

Методика

Succinic anhydride (0.60 g, 5.99 mmol, 1.1 equiv) was added in one portion to a dry THF (11 mL) solution of 3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol (2.0 g, 5.45 mmol, 1.0 equiv) and the resultant was refluxed for 18 hours under argon. The mixture was concentrated and then dissolved in EtOAc (10 mL) and poured into deionized water (20 mL). The layers were separated and the aqueous layer was extracted with two additional portions of EtOAc (25 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to provide crude 4-(3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)-4-oxobutanoic acid, a thick yellow oil, which was used without further purification.

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