Tetrahydrofuran → HCID 21905869, compound

Participants

Reaction Steps

A solution of 2-methoxyphenylmagnesium bromide is prepared from 6.8 g of magnesium in 15 ml of THF and from a solution of 52.5 g of 1-bromo-2-methoxybenzene in 75 ml of THF. This solution is added dropwise at RT, under an argon atmosphere, to a mixture of 8.9 g of 5-methyl-1H-indole-2,3-dione in 80 ml of THF and is then refluxed for 3 hours. After cooling to RT, saturated NH4Cl solution is added to the reaction mixture, the resulting mixture is extracted three times with EtOAc and the combined organic phases are washed twice with water and with saturated NaCl solution, dried over Na2SO4 and the solvent is partially concentrated. The precipitate formed is spin-filtered off to give 9 g of the expected product.

Provenance & Evidence