2-Nitrophenol → 7-(Diphenylmethoxy)-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the protected nitrophenol (3.05 g, 10 mmol) (Example 34a part i) in dry THF (100 ml) at -40° C. under nitrogen was added 1M vinyl magnesium bromide in the THF (35 ml) over 5 minutes. After stirring for a further three quarters of an hour at -40° C., the reaction mixture was poured into aqueous ammonium chloride and extracted into diethyl ether. The combined organic extracts were dried, filtered and evaporated in vacuo. The product was purified by column chromatography on silica, eluting with 12.5% ethyl acetate in hexane, to give a pale yellow solid.

Provenance & Evidence