Ethyl Acetate → HCID 57395404, compound

To a stirring ethyl acetate (100 mL) solution of 5-[[4-[(4-methoxyphenyl)methoxy]phenyl]-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (200 mg, 0.543 mmol) was added EtOH (4 mL), followed by NaBH4 (62 mg, 1.63 mmol). The reaction mixture was stirred at room temperature for 15 minutes, quenched with water (5 mL), extracted with EtOAc (10 mL). The extract was washed with brine, dried over MgSO4, filtered, and concentrated to a white solid. A solution of this white solid in 3:1 pyridine-water (5 mL) was heated at 100° C. for 24 h. The reaction mixture was cooled to room temperature and put in an ice-water bath. Concentrated HCl was carefully added to pH ˜2. The resulting suspension was extracted with ethyl acetate (10 mL×3), dried over MgSO4, filtered, and concentrated to an off-white solid. Preparative HPLC gave compound 37 as a white solid. MS ESI (neg.) m/e: 285.0 (M−1).

1. customquenched with water (5 mL)
2. extractionextracted with EtOAc (10 mL)
3. washThe extract was washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated to a white solid
7. temperatureA solution of this white solid in 3:1 pyridine-water (5 mL) was heated at 100° C. for 24 h
8. temperatureThe reaction mixture was cooled to room temperature
9. customput in an ice-water bath
10. additionConcentrated HCl was carefully added to pH ˜2
11. extractionThe resulting suspension was extracted with ethyl acetate (10 mL×3)
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. concentrationconcentrated to an off-white solid

ORD record

ord-0fe71cd1b6b440a182ce2d3a19995b70

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816367B2