Potassium Hydroxide → HCID 13934569, compound

Participants

Reaction Conditions

Reaction Steps

Diethylmalonate (4.5 g) was added to a solution of sodium metal (0.65 g) in absolute ethanol (30 ml) and the mixture was heated under reflux with stirring. 1-(2,4,6-Trimethoxy-5-pyrimidylbut-1-en-3-one (6.4 g) was added and the mixture was then boiled under reflux for 2 hours. An aqueous solution of potassium hydroxide (3.5 g in 80 ml of water) was added and the mixture was heated under reflux for a further 5 hours. The solution was cooled and extracted with chloroform (50 ml) and then the aqueous layer was heated to 90° C. and carefully acidified (pH 4.5) with dilute aqueous hydrochloric acid. The resultant precipitate was removed by filtration to give 3-hydroxy-5-(2,4,6-trimethoxy-5-pyrimidyl)cyclohex-2-en-1-one (5.2 g) as a pale yellow crystalline solid, mp 215° C. (dec). Extraction of the filtrate with ethylacetate gave a further 0.7 g of product.

Provenance & Evidence