Reacción #1121730

Ecuación de reacción

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resultant was refluxed for 18 hours under argon
2. 2
   ConcentraciónThe mixture was concentrated
3. 3
   Otrothe residue was partitioned between EtOAc (10 mL) and deionized water (20 mL)
4. 4
   OtroThe layers were separated
5. 5
   Extracciónthe aqueous layer was extracted with two additional portions of EtOAc (25 mL)
6. 6
   SecadoThe combined organic extracts were dried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

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.

Fuente