反应详情

To a mechanically stirred solution of 1H-Indole-5-carboxylic acid (5-1, 20.01 g, 124 mmol) in THF (500 mL) was added at ambient temperature slowly a solution of 1M-LAH in toluene (186 mL, 186 mmol, 1.5 equiv). The reaction mixture was heated at reflux for 1 h, quenched with ice, partitioned between ethylacetate and saturated aqueous NaHCO3. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo The crude product solidified upon standing under the reduced pressure. The crude solid was suspended in hexanes (200 mL) and ethyl acetate (10 mL), stirred overnight, collected by filtration and air-dried to afford the desired product as a light brown solid. 1H NMR (400 MHz, CDCl3) δ8.24 (br s, 1H), 7.62 (s, 1H), 7.36 (d, 1H, J=8.4 Hz), 7.23 (d, 1H, J=8.4 Hz), 7.20 (s, 1H), 6.54 (s, 1H), 4.75 (s, 2H), 1.68 (s, 1H).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 1 h
3. customquenched with ice
4. custompartitioned between ethylacetate and saturated aqueous NaHCO3
5. washThe organic layer was washed with brine
6. customseparated
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo The crude product
9. filtrationcollected by filtration
10. customair-dried