반응 #441263

반응 방정식

trifluoromethanesulfonic acid cyclohex-1-enyl ester

lithium chloride

6-methoxybenzo[b]thiophene

nBuLi

→

title compound

수율 68.1%

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

수율 68.1%

용매

THF

THF

반응 조건

후처리

1. 1
   온도was 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
   기타at room temperature
5. 5
   기타The tetrahydrofuran was removed in vacuo
6. 6
   workup.ADDITIONthe residue diluted with water
7. 7
   추출extracted with ethyl acetate
8. 8
   건조The combined organic layers was dried over anhydrous sodium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타The crude product was chromatographed on silica gel

실험 절차

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.

출처