Cerium(III) chloride → HCID 9861641, compound

To a stirred solution of 4-(3-(2,6-Dimethylbenzyloxy)phenyl)-4-oxobutyric acid (WO 02/100341, 3 g, 9.6 mmol) in methanol (64 ml) was added cerium chloride (3.55 g, 14.4 mmol). The reaction mixture was stirred for 10 minutes at room temperature, cooled to 0° C., and NaBH4 (0.400 g, 10.6 mmol) was added. The stirring continued at 0° C. for 4 hours, and the reaction was quenched with few drops of 50% aqueous acetic acid. Water (60 ml) and chloroform (60 ml) were added, and the reaction mixture was extracted with chloroform (3×25 ml). The organic layer was washed with water (2×) and brine (2×). The combined organic layer was dried over Na2SO4, filtered, concentrated and purified by flash column chromatography using chloroform:methanol (95:5 spiked with acetic acid) to give the title compound as white solid.

1. temperaturecooled to 0° C.
2. waitThe stirring continued at 0° C. for 4 hours
3. customthe reaction was quenched with few drops of 50% aqueous acetic acid
4. additionWater (60 ml) and chloroform (60 ml) were added
5. extractionthe reaction mixture was extracted with chloroform (3×25 ml)
6. washThe organic layer was washed with water (2×) and brine (2×)
7. dry with materialThe combined organic layer was dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. custompurified by flash column chromatography

ORD record

ord-131e4d74c2634e76bb2b696bf76ff787

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514555B2