Reacción #51996

Ecuación de reacción

2-methylamino-ethanol

triphenylmethyl chloride

triethylamine

→

product

Rendimiento 88.5%

2-[methyl(trityl)amino]ethanol

Rendimiento 88.5%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed in vacuum
2. 2
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (200 mL)
3. 3
   LavadoThe organic solution was washed with water (100 mL) and brine (50 mL)
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe residue was chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge
8. 8
   Lavadoeluting with 20% EtOAc in n-heptane
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

A mixture of 2-methylamino-ethanol (5.0 gr, 66.6 mmol) and triphenylmethyl chloride (18.6 g, 66.6 mmol) in 150 mL of CH2Cl2 was treated with triethylamine (9.3 mL, 66.6 mmol) and stirred at room temperature for 2 h. The solvent was removed in vacuum and the residue was dissolved in EtOAc (200 mL). The organic solution was washed with water (100 mL) and brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with 20% EtOAc in n-heptane, and those fractions with Rf=0.5 by TLC (EtOAc/hexane, 3/7) were combined and concentrated in vacuo to give 18.7 g of the product as a white solid.

Fuente