Reacción #441263

Ecuación de reacción

trifluoromethanesulfonic acid cyclohex-1-enyl ester

lithium chloride

6-methoxybenzo[b]thiophene

nBuLi

→

title compound

Rendimiento 68.1%

2-Cyclohex-1-enyl-6-methoxy-benzo[b]thiophene

Rendimiento 68.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas then warmed to room temperature for 30 minutes
2. 2
   workup.STIRRINGthe reaction was stirred at room temperature for 15 minutes
3. 3
   workup.STIRRINGthe reaction mixture was stirred for 16 hrs
4. 4
   Otroat room temperature
5. 5
   OtroThe tetrahydrofuran was removed in vacuo
6. 6
   workup.ADDITIONthe residue diluted with water
7. 7
   Extracciónextracted with ethyl acetate
8. 8
   SecadoThe combined organic layers was dried over anhydrous sodium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated
11. 11
    OtroThe crude product was chromatographed on silica gel

Procedimiento

To a solution of 6-methoxybenzo[b]thiophene (362 mg, 2.21 mmol) in 5.5 mL of THF at −20° C. was added dropwise 2.5 M nBuLi (0.97 mL, 2.4 mmol) and the reaction was stirred at 0° C. for 40 minutes and was then warmed to room temperature for 30 minutes. Next, ZnCl2 (390 mg, 2.87 mmol) in 2.5 mL of THF was added by cannula and the reaction was stirred at room temperature for 15 minutes. At this point, Pd(Ph3P)4 (102 mg), trifluoromethanesulfonic acid cyclohex-1-enyl ester (0.6 gm, 2.93 mmol)3 and anhydrous lithium chloride (0.28 gm, 6.63 mmol) were added and then the reaction mixture was stirred for 16 hrs. at room temperature. The tetrahydrofuran was removed in vacuo and the residue diluted with water and extracted with ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using hexanes as the eluant to yield 368 mg of the title compound.

Fuente