Diethyl Malonate → HCID 19047076, compound

Participants

Reaction Steps

To a solution of 0.86 g of sodium in 37 ml of absolute methanol was added 5.6 ml of diethyl malonate. After stirring for 20 minutes, the mixture was added 8 g of the 4-(2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5- yl)-3-buten-2-one in 15 ml of absolute methanol, refluxed for 4 hours and then added 75 g of 6% aqueous solution of sodium hydroxide and refluxed for 4 hours. The reaction mixture was cooled to room temperature and washed three times with 50 ml of diethyl ether. 2N aqueous solution of hydrochloric acid was added drop wise into the aqueous layer until the bubble of carbon dioxide ceased. Solid was dissolved in ethyl acetate and washed with water. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford 6.36 g of 5-(2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5-yl)cyclohexane-1,3-dione as a yellow solid.

Provenance & Evidence