反応 #1994254

反応方程式

CuCN

butadiene monooxide

phenyl magnesium bromide

phenylmagnesium bromide

→

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

溶媒

tetrahydrofuran

ether

ether

反応条件

後処理

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

実験手順

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).

出典