5-Indanol → Indole

Participants

Reaction Steps

To a solution of CDI in 25 mL anhydrous DMF was added 1 (0.76 g, 1.72 mmol), see Example 4, in one portion. The mixture was allowed to stir at room temperature for 15 minutes, then at 80° C. for 2 hours. The solution was then cooled to room temperature, the 5-indanol added, and stirring continued for 16 hours. The reaction was quenched by pouring into 200 mL H2O, and the resulting yellow precipitate filtered and air dried. Column chromatography (30% EtOAc/Hex→50% EtOAc/Hex) yielded 0.24 g (25%) of 2, mp 258°-260° C.

Provenance & Evidence