Ammonium Chloride → HCID 68289032, compound

Temperature

-78 °C

To a solution of LDA (18.8 mmol) in THF (60 mL) at −78° C. was added a solution of dimethyl 3-(4-methoxyphenyl)pentanedioate (2.0 g, 7.52 mmol) in THF (10 mL) dropwise. After stirring at −78° C. for 1 h, the dry ice-acetone bath was removed. The reaction mixture was stirred for 30 min before being cooled to −78° C. Solid AgCl (2.2 g, 15.4 mmol) was added all at once. The reaction mixture was stirred at −78° C. for 1 h and then room temperature overnight. Saturated aqueous NH4Cl was added. The mixture was vigorously stirred for 10 min. The suspension was filtered through celite. The filtrate was extracted with EtOAc (3×). The combined organic extract was dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography with EtOAc in hexane (10%, 15%, 20%, then 30%) to give the title compound as a pale yellow solid (0.87 g, 44% yield). 1HNMR (CDCl3, 400 Hz) δ 7.09 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 3.82 (s, 3H), 3.77 (s, 6H), 3.17 (t, J=7.6 Hz, 1H), 2.36 (d, J=7.6 Hz, 2H).

1. customthe dry ice-acetone bath was removed
2. stirringThe reaction mixture was stirred for 30 min
3. temperaturebefore being cooled to −78° C
4. stirringThe reaction mixture was stirred at −78° C. for 1 h
5. customroom temperature overnight
6. stirringThe mixture was vigorously stirred for 10 min
7. filtrationThe suspension was filtered through celite
8. extractionThe filtrate was extracted with EtOAc (3×)
9. extractionThe combined organic extract
10. dry with materialwas dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by flash column chromatography with EtOAc in hexane (10%, 15%, 20%

ORD record

ord-0c990ae534fb42928e68e5f6ef988776

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2