Ethyl Acetate → HCID 178422298, compound

Temperature

-78 °C

In a 20 mL scintillation vial, Compound [IV] (0.15 g, 0.543 mmol, 1.0 eq.) was dissolved in THF (10 mL). The solution was cooled to −78° C. and MeLi (15 mL of 1.6 M THF solution, 24 mmol, 44.19 eq.) was added dropwise and the reaction mixture was stirred for 16 hours at 0-20° C. The reaction mixture was carefully and slowly poured into ethyl acetate 20 (mL) and stirred for 10 minutes. The quenched reaction mixture was concentrated. The residue was treated with 100 mL of THF and the THF solution was separated from the solid by filtration. The organic solution was stirred with MnO2 (0.47 g, 5.4 mmol, 10 eq.) for 4 hours at room temperature. The reaction was filtered and the solids washed with CHCl3/MeOH (10%) (50 mL). The combined organic solution was concentrated and the crude was purified by silica gel chromatography using CHCl3/MeOH (10%) as the eluant to give Compound [CIX]: LCMS m/e 291 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.51 (s, 3H) 2.77 (s, 3H) 6.40 (s, 1H) 7.36-7.51 (m, 3H) 7.71 (d, J=7.22 Hz, 2H) 7.97 (s, 1H).

1. stirringstirred for 10 minutes
2. customThe quenched reaction mixture
3. concentrationwas concentrated
4. additionThe residue was treated with 100 mL of THF
5. customthe THF solution was separated from the solid by filtration
6. filtrationThe reaction was filtered
7. washthe solids washed with CHCl3/MeOH (10%) (50 mL)
8. concentrationThe combined organic solution was concentrated
9. customthe crude was purified by silica gel chromatography
10. customto give Compound [CIX]

ORD record

ord-7ee0ec834f7e42ef8643ada69744b01b

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614221B2