p-Isopropylphenyl isocyanate → 1-Benzylindolin-5-yl 4-isopropylphenylcarbamate

Participants

Reaction Steps

To a solution of 1-benzylindolin-5-ol (1.50 g, 6.66 mmol) in 33 mL of diethyl ether (5 mL/mmol) was added a piece of sodium (1 mg to 10 mg) at room temperature. After the reaction mixture was stirred at the same temperature for 2 min, 4-isopropylphenylisocyanate (1.3 mL, 8.0 mmol, 1.2 equivalent) was added with additional stirring for 5 min to 10 min. After removal of sodium, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 0/100) to obtain the title compound (2.24 g, 87%) as a white solid.

Provenance & Evidence