Reaktion #1121730

Reaktionsgleichung

Succinic anhydride

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

→

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resultant was refluxed for 18 hours under argon
2. 2
   EinengenThe mixture was concentrated
3. 3
   Sonstigethe residue was partitioned between EtOAc (10 mL) and deionized water (20 mL)
4. 4
   SonstigeThe layers were separated
5. 5
   Extraktionthe aqueous layer was extracted with two additional portions of EtOAc (25 mL)
6. 6
   TrocknenThe combined organic extracts were dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

Succinic anhydride (0.60 g, 5.99 mmol, 1.1 equiv) was added in one portion to a dry THF (11 mL) solution of 1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-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 the residue was partitioned between EtOAc (10 mL) and 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-(1-(dimethylamino)-4-((9Z,12Z)-octadeca-9,12-dienyloxy)butan-2-yloxy)-4-oxobutanoicacid, a thick, yellow oil, which was used without further purification.

Quelle