2-Methyl-3-butyn-2-ol → 4-(1H-indol-5-yl)-2-methyl-but-3-yn-2-ol

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Reaction Steps

A mixture of 5-iodoindole (25 g, 102.9 mmol), triphenylphosphine (2.70 g, 10.3 mmol), CuI (1.96 g, 10.3 mmol), potassium carbonate (35.5 g, 257.2 mmol), palladium (5 wt. % on calcium carbonate, poisoned with lead) (0.55 g, 5.14 mmol) and 1,2-dimethoxyethane (250 ml) was stirred at room temperature for 0.5 hour. 2-Methyl-3-butyn-2-ol (21.6 g, 257 mmol) was added and the mixture was stirred for 15 hours at 100° C. The crude mixture was filtered through silica gel and aqueous hydrochloric acid (250 ml, 2 M) was added and extracted with toluene. The organic phase was dried and evaporated. Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound. Yield 6.7 g (33%). Mp. 119-123° C.

Provenance & Evidence