Boron trifluoride → 3-Carboethoxy-1,8,8-trimethylbicyclo[3,2,1]octane-2,4-dione

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Reaction Steps

To a solution of (±) camphorquinone [(1,7,7)-trimethylbicyclo[3,2,1]-heptane-2,3-dione] (15.0 g, 90.24 mmol) and ethyl diazoacetate (11.8 g, 103.7 mmol) in 120 ml of ether is added, at 0°, BF3.ether (4 ml). The mixture is stirred at RT for 24 hr. The reaction mixture is extracted with 5% K2CO3 /H2O until no polar ethyl carboxyl dione remains. The combined aqueous extracts are acidified with conc. HCl and extracted with ether. The combined organic extracts are dried and evaporated to dryness to give crystalline 3-carboethoxy-1,8,8-trimethylbicyclo[3,2,1]octane-2,4-dione.

Provenance & Evidence