Reacción #462276

Ecuación de reacción

3-aminobenzyl alcohol

tert-butyldimethylsilyl chloride

triethylamine

→

3-(O-t-butyldimethylsilyloxymethyl)aniline

Rendimiento 57.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas then partitioned between ethyl acetate and H2O
2. 2
   LavadoThe organic phase was washed twice with H2O, twice with brine
3. 3
   Secadodried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of 3-aminobenzyl alcohol (2.00 g, 16.2 mmol) and tert-butyldimethylsilyl chloride (2.90 g, 19.4 mmol) in CH2Cl2 (32.5 mL) was added triethylamine (7.45 mL, 53.5 mmol). The reaction mixture was stirred for 18 hours at ambient temperature and was then partitioned between ethyl acetate and H2O. The organic phase was washed twice with H2O, twice with brine, dried over MgSO4, filtered, and concentrated in vacuo. 3-(O-t-butyldimethylsilyloxymethyl)aniline (2.18 g, 57%) was obtained as a yellow oil by chromatography on silica gel (30% ethyl acetate/hexane). 1H NMR (300 MHz, CDCl3) δ7.10 (1H, t, J=7.5 Hz), 6.67-6.72 (2H, m), 6.56 (1H, br d, J=7.5 Hz), 4.66 (2H, s), 3.63 (2H, br s), 0.94 (9H, s), 0.09 (6H, s). MS m/e 238 (M+H)+, 255 (M+NH4)30 .

Fuente