α-CCN- synthesis
- Product Name:α-CCN-
- CAS Number:14378-06-4
- Molecular formula:C10H7NO2
- Molecular Weight:173.17
Yield:14378-06-4 71%
Reaction Conditions:
with diphenyl(methyl)phosphine in toluene at 20; for 16 h;Schlenk technique;Inert atmosphere;stereoselective reaction;
Steps:
General procedure for trans hydrocyanation of 3-phenylpropiolic acids
(E)-2-cyano-3-phenylacrylic acid (2r). 3-phenylpropiolic acid 1r (2.5 mmol, 1 eq) and toluene (2.5 mL) were mixed together under atmosphere of nitrogen, in test tube previously dried under vacuum. While gentle stirring, TMSCN was added (3 mmol, 1.2 eq), which was followed by dissolution of the acid (DANGER: hydrogen cyanide is formed in this reaction and the reaction must be conducted in the fume hood with proper ventilation). After acid was dissolved and PPh2Me (10 mol %) was added, reaction mixture was stirred at room temperature for 16 hours. Reaction was quenched with water (3 mmol, 1.2 eq) and venously stirred for 10 minutes. Formed precipitate was filtered under vacuum, washed with cold toluene and dried under vacuum to give clean product 2r in form of white crystals, without further purification (307 mg, 71 %)
References:
Sch?mberg, Fritz;Peri?, Milica;Meyer, Maximilian;Vilotijevi?, Ivan [Tetrahedron,2021,vol. 99,art. no. 132457] Location in patent:supporting information
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