Hydrochloric Acid → (1S, 2R)-1-phenyl-2-hydroxymethylcyclopropane carboxylic anhydride

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Reaction Steps

8.58 g (0.22 mol ) of sodium amide was suspended in 40 ml of anhydrous benzene, to thereby obtain a suspension. To the obtained suspension was dropwise added a solution of 11.5 ml (0.10 mol) of phenylacetonitrile in 20 ml of anhydrous benzene in a stream of argon gas at 0° C. Then, the resultant mixture was stirred at room temperature for 3 hours, to thereby effect a reaction. To the reaction mixture was dropwise added a solution of 6.8 ml (0.087 mol) of a racemic modification of epichlorohydrin in 20 ml of anhydrous benzene while cooling with ice. Then, the resultant mixture was stirred at room temperature for 2 hours to thereby effect a reaction. After completion of the reaction, the reaction mixture was subjected to distillation under reduced pressure to thereby remove the solvent and obtain a residue. To the obtained residue were added 20 ml of ethanol and 10 ml of an aqueous 1N-KOH solution to thereby obtain a mixture. The mixture was refluxed for 15 hours. After that period of time, 12N hydrochloric acid was added to the resultant mixture while cooling with ice to thereby acidify the mixture. The acidified mixture was concentrated under reduced pressure to thereby obtain a residue. A saturated aqueous sodium hydrogencarbonate solution was added to the obtained residue, and ethyl acetate was further added for extraction to obtain an organic layer. The organic layer was separated, washed with saturated saline, dried over anhydrous sodium sulfate, and subjected to distillation under reduced pressure to thereby remove the solvent and obtain a residue. The obtained residue was purified by silica gel column chromatography (the composition of the developing solvent was; ethyl acetate:hexane=1:3). As a result, compound 25 (yield: 60%) was obtained as an orange oily product.

Provenance & Evidence