Water → 2,2-Dimethyl-3-phenylcyclopropanecarbonitrile

Participants

Reaction Steps

A mixture of 234 mg (0.96 mmole) of cyclopropanoid cyanoester 10 (produced in accordance with Example VIII), 174 mg (2.1 mmoles) of sodium bicarbonate, and 35 mg of water in 2.0 mL of 1,3-propanediol was heated at reflux, protected from atmospheric moisture, for 45 minutes. The product was isolated by diluting the cooled mixture with 25 mL of saturated brine and extraction with ether. The ether extracts were washed in successive order with 20 mL of 1:1 (v/v) 1M aqueous NaOH:saturated brine and 20 mL of 10% aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. Removal of the ether by evaporation at reduced pressure afforded 157 mg (95% yield) of nitrile 17 as a mixture of cis and trans stereoisomers, subsequently shown by NMR analysis (vinyl H absorption at approximately 5.0δ) to be accompanied by a minor amount (~10-15%) of ring-opened by-product.

Provenance & Evidence