Reaction #1994254

Reaction equation

CuCN

butadiene monooxide

phenyl magnesium bromide

phenylmagnesium bromide

→

trans-4-phenyl-2-butene-1-ol

Solvents

tetrahydrofuran

ether

ether

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   Temperatureto warm to 0° C.
3. 3
   workup.STIRRINGto stir until the reaction mixture
4. 4
   workup.WAITAfter this period
5. 5
   Temperaturethe reaction mixture was cooled to −78° C.
6. 6
   Temperatureto warm to 23° C. for 1 h
7. 7
   OtherThe reaction was quenched by slow addition of saturated aqueous NH4Cl (120 mL)
8. 8
   ExtractionThe aqueous layer was thoroughly extracted with ethyl acetate (2×300 mL)
9. 9
   DryingThe combined organic layers were dried over anhydrous Na2SO4
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated under reduced pressure
12. 12
    workup.DISTILLATIONThe residue was distilled under vacuum (0.12 torr) at 95° C.

Procedure

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).

Source