1-Cyclohexenyl trifluoromethanesulfonate → 6-Methoxy-2-(1-cyclohexenyl)benzo[b]thiophene

Temperatur

0 °C

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.

1. temperaturewas then warmed to room temperature for 30 minutes
2. stirringthe reaction was stirred at room temperature for 15 minutes
3. stirringthe reaction mixture was stirred for 16 hrs
4. customat room temperature
5. customThe tetrahydrofuran was removed in vacuo
6. additionthe residue diluted with water
7. extractionextracted with ethyl acetate
8. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude product was chromatographed on silica gel

ORD-Eintrag

ord-387e9b46e1da444aafb6a63060ec9a88

Quelldatensatz

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06756388B1