تفاعل #1443476

معادلة التفاعل

6-fluoro-3-indoleglyoxylic acid ethyl ester

LiAlH4

H2O

KOH

H2O

→

title compound

2-(6-fluoro-1H-indol-3-yl)-ethanol

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed for 3 h
2. 2
   ترشيحThe mixture was filtered
3. 3
   workup.ADDITIONThe filtrate was diluted with EtOAc
4. 4
   غسيلwashed with H2O and brine
5. 5
   تجفيفThe EtOAc solution was dried
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated

الإجراء التجريبي

To a solution of 6-fluoro-3-indoleglyoxylic acid ethyl ester (2.01 g, 8.55 mmol) in dry THF (0.11 L) at 0° C. under argon was added LiAlH4 (1.68 g, 44.2 mmol). The reaction mixture was refluxed for 3 h, cooled to 0° C., and treated with H2O (1.7 mL), 15% aq KOH (1.7 mL), and H2O (5 mL). The mixture was filtered. The filtrate was diluted with EtOAc, and washed with H2O and brine. The EtOAc solution was dried, filtered, and concentrated to give the title compound: TLC Rf=0.33 (9:1 CH2Cl2/Me2CO); MS (ESI−) m/z 178.0; 1H NMR (CDCl3, 300 MHz) δ 8.38 (1H), 7.49 (1H), 7.01-6.63 (3H), 3.90 (2H), 2.99 (2H), 2.23 (1H).

المصدر