Sodium Dithionite → HCID 22238098, compound

Participants

Reaction Steps

To a solution of 1,4-dimethoxy-2,3-dimethyl-5-(2-nitro-1-propenyl)benzene (2.51 g, 9.99 mmol) in THF (35 mL) was added lithium aluminum hydride (1.0 g, 26 mmol) under ice-cooling, and the mixture was heated to reflux for 6 hours. Hyflo Super-Cel® (5 g) was added to the reaction mixture, and water (1.5 mL) was added dropwise under ice-cooling. The resulting mixture was suspended in ethyl acetate, filtered, concentrated under the reduced pressure to obtain an oil. This was dissolved in acetonitrile (10 mL), a solution of diammonium cerium (IV) nitrate (10.9 g, 19.9 mmol) in acetonitrile (20 mL) and water (20 mL) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, neutralized with sodium bicarbonate and extracted with ethyl acetate three times. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the solid. This was dissolved in ethyl acetate, mixed with an aqueous solution of sodium hydrosulfite, shaken, and the precipitated solid was filtered to obtain 0.79 g of 2,3-dihydro-2,6,7-trimethyl-1H-indole-5-ol.

Provenance & Evidence