moles of sodium hydride was added after another 4 hours of stirring at reflux the reaction was filtered the collected solid excess nah was destroyed by the cautious addition of ethanol the filtrate was cooled to 0 u00b0 c and the product slowly precipitated out the solution may need some agitation to get product to precipitate as it has a tendency to supersaturate the product was collected by filtration and dried to give 16 2 g of a slightly yellow solid 97 yield the solid is hydroscopic and slowly turned to a sticky orange material the 1 h nmr consisted of a mixture of enol and keto tautomers 1 h nmr dmso d 6 u03b49 2 h2 39 keto s 8 75 h2 39 h6 39 enol m 8 6 h6 39 keto d 8 3 h4 39 keto d 7 85 h4 39 enol d 7 4 h5 39 keto dd 7 3 h5 39 enol dd 4 4 ch keto t 4 25 n ch 2 n enol s 4 15 nch 2 n keto d 3 45 m 2 6 ch 2 ch 3 m 2 5 m 2 2 m 2 05 m 1 8 m and 1 05 m ch 3 the sodium salt 2 900 mg 2 90 mmoles was heated at reflux for 12 hours in a 5 1 mixture of concentrated hcl and acetone the acetone was required in order to give product of better quality the reaction was allowed to cool and nacl was filtered off the filtrate was diluted with 70 ml of isopropyl alcohol and.