반응 #1994254

반응 방정식

CuCN

butadiene monooxide

phenyl magnesium bromide

phenylmagnesium bromide

→

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

용매

tetrahydrofuran

ether

ether

반응 조건

후처리

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

실험 절차

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).

출처