[Na].C(OCC)(=O)[CH2:3][C:4](OCC)=[O:5].[CH2:13]([S:15][CH:16]([CH3:23])[CH2:17][CH:18]=[CH:19][C:20](=[O:22])[CH3:21])[CH3:14].[OH-].[Na+].Cl>O.C(O)C>[CH2:13]([S:15][CH:16]([CH3:23])[CH2:17][CH:18]1[CH2:3][C:4](=[O:5])[CH2:21][C:20](=[O:22])[CH2:19]1)[CH3:14]
2.53 g of metallic sodium were added to 100 ml of ethanol at room temperature. To this was then added 17.6 g of diethyl malonate, with stirring, and then 17.2 g of 6-ethylthio-3-hepten-2-one was added. The resulting mixture was then refluxed for four hours and then an aqueous sodium hydroxide solution, containing 9.5 g of sodium hydroxide in 75 ml of water, was added and the mixture refluxed for another two hours. The mixture was cooled to 50° C. and then acidified by the addition of concentrated hydrochloric acid. The mixture was then warm until decarboxylation was complete and then evaporated to a liquid residue. The residue was mixed with ethyl ether, washed with water, and evaporated to a brown liquid. The liquid was base, acid extracted affording 5-(2-ethylthiopropyl) cyclohexane-1,3-dione.
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