2-Nitropropane → Ethyl 1-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylate

関与物質

反応手順

A mixture of 534 mg (2.65 mmoles) of cyanoester 1 (produced in accordance with Example I), 0.25 mL (2.78 mmoles) of 2-nitropropane, and 4.0 mL (2.60 mmoles of sodium ethoxide) of an 0.65M solution of sodium ethoxide (prepared from sodium metal and ethyl alcohol) in ethyl alcohol was stirred at room temperature for 10 minutes and subsequently heated at gentle reflux, protected from atmospheric moisture, for 3 hours. The product was isolated by cooling the mixture to room temperature, diluting it with 30 mL of 10% aqueous sodium chloride, and extraction with dichloromethane. The dichloromethane extracts were washed with 10% aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. Removal of the dichloromethane at reduced pressure, followed by evaporative distillation, [bath temperature: 125°-135° C. (0.05 mm)], afforded 620 mg (96% yield) of cyclopropanoid cyanoester 10. The presence of a single sharp peak (δ3.30) for the cyclopropyl H in 10 suggested the presence of only one stereoisomer (neglecting optical isomerism)--the phenyl and cyano substituents being cis, as shown by subsequent decarbalkoxylation results).

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