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温度

0 °C

To a suspension of LiAlH4 (8.60 g, 0.23 mole) in 400 mL of dry THF was added 5-fluoro-3-indoleglyoxylic acid ethyl ester (13.50 g, 0.057 mole) portionwise at room temperature. Preparation of this ester intermediate is given hereinbelow. The mixture was heated to reflux under Ar for 1 h and was then cooled at 0° C. and quenched according to the method of Fieser (Fieser and Fieser, "Reagents for Organic Synthesis", Vol. 1, pg. 584). The resulting slurry was filtered and the filter cake was washed with THF. The filtrate was dried (Na2SO4) and evaporated to give the product (10.00 g, 100%) as a yellow oil. It was used as such without further purification; IR (neat) 3420 cm-1. 1Hnmr (80 MHz, CDCl3). δ: 7.73 (br s, 1H), 7.1-6.4 (m, 4H), 3.57 (t, J=8 Hz, 2H), 2.66 (t, J=8 Hz, 2H), 1.20 (br s, 1H).

1. temperatureThe mixture was heated
2. temperatureto reflux under Ar for 1 h
3. customquenched
4. customaccording to the method of Fieser (Fieser and Fieser, "Reagents for Organic Synthesis", Vol. 1, pg. 584)
5. filtrationThe resulting slurry was filtered
6. washthe filter cake was washed with THF
7. dry with materialThe filtrate was dried (Na2SO4)
8. customevaporated