反应详情

In an oven dried 1 neck round bottom flask with reflux condenser and stirbar, trans-4-carbomethoxycyclohexane-1-carboxylic acid (840 mg; 4.5 mmol) was heated to reflux in the presence of 15 mL thionyl chloride. After 3 hours reflux, mixture cooled to 40° C. under nitrogen flow, and excess thionyl chloride was removed at reduced pressure. Residue was taken up in 5 mL of dry tetrahydrofuran and added to a 0° C. mixture of 2-fluorophenylzinc iodide (9.0 mL; 4.5 mmol), tetrakis(triphenylphospine)palladium (0) (272 mg; 0.2 mmol) in 10 mL anhydrous tetrahydrofuran. Mixture was allowed to warm to room temperature over 16 hours. Reaction was quenched with 6 mL 1N HCl and ethyl acetate was taken in. Organics separated and aqueous re-extracted with 20 mL ethyl acetate. Combined organics were washed with sat. NaHCO3, water, brine and dried over MgSO4. Material was purified via flash silica plug (10:1) using 15% ethyl acetate in hexanes isocratic to give 800 mg of title compound. (67% yield)

1. customIn an oven dried 1 neck round bottom flask
2. temperaturewith reflux condenser
3. temperatureAfter 3 hours reflux
4. customwas removed at reduced pressure
5. additionadded to a 0° C.
6. customReaction
7. customwas quenched with 6 mL 1N HCl and ethyl acetate
8. customOrganics separated
9. extractionaqueous re-extracted with 20 mL ethyl acetate
10. washCombined organics were washed with sat. NaHCO3, water, brine
11. dry with materialdried over MgSO4
12. customMaterial was purified via flash silica plug (10:1)