Réaction #1121728

Équation de réaction

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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températurethe resultant was refluxed for 18 hours under argon
2. 2
   ConcentrationThe mixture was concentrated
3. 3
   workup.DISSOLUTIONdissolved in EtOAc (10 mL)
4. 4
   workup.ADDITIONpoured into deionized water (20 mL)
5. 5
   AutreThe layers were separated
6. 6
   Extractionthe aqueous layer was extracted with two additional portions of EtOAc (25 mL)
7. 7
   SéchageThe combined organic extracts were dried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated

Mode opératoire

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.

Source