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

Beteiligte Stoffe

Reaktionsschritte

8.58 g (0.22 mol) of sodium amide was suspended in 40 ml of anhydrous benzen. To the resultant suspension was dropwise added a solution of 11.5 ml (0.10 mol) of phenylacetonitrile in 20 ml of anhydrous benzen in a stream of argon gas at 0° C. After the addition, the resultant mixture was stirred at room temperature for 3 hours to effect a reaction. To the resultant mixture was dropwise added a solution of 6.8 ml (0.087 mol) of (S)-(+)-epichlorohydrin in 20 ml of anhydrous benzen while cooling with ice. After the addition, the resultant mixture was stirred at room temperature for 2 hours to effect a reaction. After completion of the reaction, the resultant 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. The resultant mixture was refluxed for 15 hours to effect a reaction. After completion of the reaction, 12N hydrochloric acid was added to the resultant reaction mixture to thereby acidify the mixture, and 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 residue was purified by silica gel column chromatography (the composition of the developing solvent was; ethyl acetate:hexane=1:3). As a result, compound 13 (10.0 g) was obtained as an orange oily product.

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