Réaction #1994254
ord-037edaeb5985468187d567d764355c27
Équation de réaction
Réactifs
Solvants
Conditions de réaction
Traitement
- 1AutreThe resulting reaction mixture
- 2Températureto warm to 0° C.
- 3workup.STIRRINGto stir until the reaction mixture
- 4workup.WAITAfter this period
- 5Températurethe reaction mixture was cooled to −78° C.
- 6Températureto warm to 23° C. for 1 h
- 7AutreThe reaction was quenched by slow addition of saturated aqueous NH4Cl (120 mL)
- 8ExtractionThe aqueous layer was thoroughly extracted with ethyl acetate (2×300 mL)
- 9SéchageThe combined organic layers were dried over anhydrous Na2SO4
- 10Filtrationfiltered
- 11Concentrationconcentrated under reduced pressure
- 12workup.DISTILLATIONThe residue was distilled under vacuum (0.12 torr) at 95° C.
Mode opératoire
Anhydrous CuCN (4.86 g, 54 mmol) was added to a solution of butadiene monooxide (38 g, 540 mmol) in anhydrous tetrahydrofuran (1.2 L) and the resulting mixture was stirred at −78° C. Commercial phenyl magnesium bromide solution (Aldrich) in ether (65 mmol) was added dropwise over a period of 10 min. The resulting reaction mixture was then allowed to warm to 0° C. and it was continued to stir until the reaction mixture was homogeneous. After this period, the reaction mixture was cooled to −78° C. and 0.58 mole of phenylmagnesium bromide solution in ether was added dropwise for 30 min. The reaction mixture was allowed to warm to 23° C. for 1 h. The reaction was quenched by slow addition of saturated aqueous NH4Cl (120 mL) followed by NH4OH (70 mL), saturated NH4Cl (500 mL) and then H2O (300 mL). The aqueous layer was thoroughly extracted with ethyl acetate (2×300 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was distilled under vacuum (0.12 torr) at 95° C. to give trans-4-phenyl-2-butene-1-ol (75.6 g).