Reacción #607401

Ecuación de reacción

2-amino-2-(4-chloro-3-methylphenyl)acetic acid

lithium aluminum hydride

→

title compound

Rendimiento 101.4%

2-amino-2-(4-chloro-3-methylphenyl)ethanol

Rendimiento 101.4%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was refluxed for 18 hours
2. 2
   TemperaturaThe reaction was cooled
3. 3
   Otroquenched with ice water
4. 4
   ExtracciónThe reaction was extracted with ethyl acetate
5. 5
   Lavadowashed with water, and brine
6. 6
   SecadoThe combined organic layers were dried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

To 2-amino-2-(4-chloro-3-methylphenyl)acetic acid (1.7 g, 8.5 mmol) in tetrahydrofuran (0.4 M) at 0° C. was added lithium aluminum hydride (2 M, 8.5 mL, 17 mmol) dropwise. The reaction was refluxed for 18 hours. The reaction was cooled and quenched with ice water. The reaction was extracted with ethyl acetate, washed with water, and brine. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to provide the title compound as a yellow solid (1.6 g, quantitative): 1H NMR (300 MHz, DMSO-d6) δ 7.44-7.23 (m, 2H), 7.18 (dd, J=8.2, 2.2 Hz, 1H), 4.77 (bs, 2H), 3.81 (dd, J=7.8, 4.8 Hz, 1H), 3.53-3.14 (m, 3H), 2.30 (s, 3H); ESIMS m/z 186 ([M+H]+).

Fuente