Oxygen → ethyl 2-(adamantan-1-yl)acetate

Participants

Reaction Steps

A mixture of 10 mmol of ethyl acrylate, 50 mmol of adamantane, 1 mmol of N-hydroxyphthalimide, 0.01 mmol of cobalt(II) acetate, 0.1 mmol of acetylacetonatocobalt(III), and 54 mmol of acetonitrile was stirred at 70° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was concentrated, and the concentrate was subjected to column chromatography on a silica gel to yield ethyl 3-(adamant-1-yl)-2-hydroxypropionate of the following formula (a), ethyl 3-(adamant-1-yl)-2-oxopropionate of the following formula (b), and ethyl 1-adamantaneacetate of the following formula (c) in yields of 55%, 16%, and 8%, respectively. The conversion rate from ethyl acrylate was 99%.

Provenance & Evidence