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note
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General procedure for the synthesis of 3-alkoxy-3-cyano carboxylic acids 2: To a solution of the enones 1 (5.0 mmol) in THF (3.0 mL) a solution of sodium cyanide (0.24 g, 5.0 mmol) in water (3.0 mL) was added, under stirring, at room temperature. The reaction mixture was stirred for 30 min and a new addition of a solution of sodium cyanide (0.24 g, 5.0 mmol) in water (3 mL) was added and the stirring was continued for 1-6 h, at room temperature. The products 2a-h were isolated through two extractions; in the first, the pH is basic from the reaction (pH ∼10) and the solution was extracted with ethyl ether (2 × 20 mL) to eliminate possible unreacted starting material. In the second extraction, the pH was lowered to about three with the addition of 1 M solution of hydrochloric acid and the solution was extracted with ethyl ether (2 × 20 mL) to recover the products 2a-h in the organic phase. The organic phase was dried under magnesium sulfate, filtered, and the solvent was evaporated to render 3-alkoxy-3-cyanocarboxylic acids 2a-h, as oils, in good yields, and high purity.
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Zanatta N., Schneider J.M.F.M., Schneider P.H., Wouters A.D., Bonacorso H.G., Martins M.A.P., and Wessjohann L.A. J. Org. Chem. 71 (2006) 6996
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Bonacorso, H.G.5
Martins, M.A.P.6
Wessjohann, L.A.7
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2),...
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0242487852
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Martins M.A.P., Pereira C.M.P., Zimmermann N.K.E., Moura S., Sinhorin A.P., Cunico W., Zanatta N., Bonacorso H.G., and Flores A.F.C. Synthesis (2003) 2353
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Martins, M.A.P.1
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Cunico, W.6
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Bonacorso, H.G.8
Flores, A.F.C.9
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0001048708
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Stevens R.V., Christensen C.G., Edmonson W.L., Kaplan M., Reid E.B., and Wentland M.P. J. Am. Chem. Soc. 93 (1971) 6629
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