Réaction #607401

Équation de réaction

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

lithium aluminum hydride

→

title compound

Rendement 101.4%

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

Rendement 101.4%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was refluxed for 18 hours
2. 2
   TempératureThe reaction was cooled
3. 3
   Autrequenched with ice water
4. 4
   ExtractionThe reaction was extracted with ethyl acetate
5. 5
   Lavagewashed with water, and brine
6. 6
   SéchageThe combined organic layers were dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Mode opératoire

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]+).

Source