Iodine → HCID 68719179, compound

To a cold (−78° C.) solution of Example 48A (500 mg, 3.26 mmol) in tetrahydrofuran (50 mL) was added n-butyllithium (4.08 mL, 6.53 mmol, 1.6M in hexane) dropwise. After stirring for 30 min, a solution of iodine (0.829 g, 3.26 mmol) in tetrahydrofuran (5 mL) was added dropwise. After 2 h, the reaction was quenched by the addition of 10% Na2S2O3 solution (10 mL) and ethyl acetate (10 mL) and warmed to room temperature. The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×50 mL). The combined organics were washed with brine (1×50 mL), dried over Na2SO4, concentrated under reduced pressure, and purified by chromatography on SiO2 gel, eluting with 50% ethyl acetate in hexane, to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.65 (s, 2H), 1.79 (s, 2H), 1.89 (s, 2H), 2.02 (s, 2H), 5.50 (s, 1H), 7.22 (s, 1H).

1. waitAfter 2 h
2. customthe reaction was quenched by the addition of 10% Na2S2O3 solution (10 mL) and ethyl acetate (10 mL)
3. customThe layers were separated
4. extractionthe aqueous was extracted with additional ethyl acetate (2×50 mL)
5. washThe combined organics were washed with brine (1×50 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. custompurified by chromatography on SiO2 gel
9. washeluting with 50% ethyl acetate in hexane

ORD record

ord-17befc2461684889b0559dc66c412403

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242139B2