Iodoethane → 2-Ethyl-2-adamantanol

Participants

Reaction Steps

To 5 mL of ether was added 3.7 g (0.15 gram atom) of magnesium. To the mixture was added dropwise a solution of ethyl iodide (30 g, 0.19 mol) in ether (30 mL). The solution of ethylmagnesium iodide thus prepared was added dropwise to a solution of 2-adamantanone (20 g, 0.13 mol) in tetrahydrofuran (100 ml), and the mixture was stirred at room temperature overnight. GC analysis indicated that reduction products, i.e., 2-adamantanol and 2-ethyl-2-adamantanol were formed in 75% and 25%, respectively.

Provenance & Evidence