Reacción #1121727

Ecuación de reacción

TBAF

3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine

→

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated
2. 2
   Otrothe residue was partitioned between EtOAc (15 mL) and aqueous saturated ammonium chloride solution (10 mL)
3. 3
   OtroThe layers were separated
4. 4
   Extracciónthe aqueous layer was extracted with 2 additional portions of EtOAc (10 mL)
5. 5
   SecadoThe combined extracts were dried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated

Procedimiento

TBAF (1.0 M in THF, 0.5 mL, 0.50 mmol, 1.2 equiv) was added in one portion to a dry THF (100 μL) solution of 3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine (0.2 g, 0.42 mmol, 1.0 equiv) and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated and the residue was partitioned between EtOAc (15 mL) and aqueous saturated ammonium chloride solution (10 mL). The layers were separated and the aqueous layer was extracted with 2 additional portions of EtOAc (10 mL). The combined extracts were dried (MgSO4), filtered, and concentrated to give crude 3-(dimethylamino)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol, a thick, beige oil, which was used without further purification.

Fuente