Hydrochloric Acid → HCID 69735993, compound

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Reaction Steps

Methylmalonic acid diethylester (1.57 g, 9.02 mmol) was dissolved in dimethylformamide (30 ml), and sodium hydride (0.38 g, 9.47 mmol) was added thereto in an ice bath, and then the mixture was stirred for 1 hour at room temperature in a nitrogen atmosphere. The dimethylformamide solution (30 ml) of 2-(2-iodoethyl)-4-(5-phenylpent-1-ynyl)thiophene obtained in Example 25 (e) was added dropwise to the reaction solution in an ice bath, and the mixture was stirred for 4 hours at room temperature under a nitrogen atmosphere. After the reaction solution was cooled down, acidified with 1N hydrochloric acid, and the resulting solution was extracted with ethyl acetate, and then the ethyl acetate layer was washed with a 1N aqueous sodium hydroxide solution and then with a saturated aqueous sodium chloride solution. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The residue was partially purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=50:1-20:1). The obtained mixture was dissolved in a mixture of ethanol (9 ml) and water (1 ml), and potassium hydroxide (0.80 g, 14.3 mmol) was added thereto in an ice bath, and then the reaction mixture was stirred for 3 days at room temperature. After the reaction solution was acidified with 1N hydrochloride acid, the resulting solution was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; dichloromethane:methanol=50:1) to afford the title compound (1.02 g, 28% yield).

Provenance & Evidence