Reaktion #607401

Reaktionsgleichung

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

lithium aluminum hydride

→

title compound

Ausbeute 101.4%

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

Ausbeute 101.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was refluxed for 18 hours
2. 2
   TemperaturThe reaction was cooled
3. 3
   Sonstigequenched with ice water
4. 4
   ExtraktionThe reaction was extracted with ethyl acetate
5. 5
   Waschenwashed with water, and brine
6. 6
   TrocknenThe combined organic layers were dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

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]+).

Quelle