Reaction #1121728

Reaction equation

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

Solvents

THF

Conditions

Workup

1. 1
   Temperaturethe 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
   OtherThe layers were separated
6. 6
   Extractionthe aqueous layer was extracted with two additional portions of EtOAc (25 mL)
7. 7
   DryingThe combined organic extracts were dried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated

Procedure

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