1533440-50-4 → HCID 90022344, compound

Into a 250-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen and containing THF (60 mL), was placed a solution of ethylmagnesium bromide (3 M in diethyl ether) (24.6 mL, 73.8 mmol). A solution of 4-cyclopropyl-3-formylbenzoic acid (compound 10.4, 3.5 g, 18.4 mmol) in THF (40 mL) was added drop-wise at room temperature over 45 min. The resulting mixture was stirred for 1.5 h at room temperature, then carefully quenched with water/ice (50 mL). The mixture was diluted with EtOAc (100 mL) and the organic layer was washed with aqueous NH4Cl (sat., 2×100 mL) and the aqueous layers combined. The pH of the aqueous phase was adjusted to 3-4 with aqueous hydrogen chloride (2 M) and extracted with ethyl acetate (2×150 mL). The combined organic extracts were washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate:PE (1:10-2:1) as the eluent to yield 3.4 g (84%) of the title compound as a white solid.

1. customInto a 250-mL 3-necked round-bottom flask, purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. additioncontaining THF (60 mL)
4. customcarefully quenched with water/ice (50 mL)
5. additionThe mixture was diluted with EtOAc (100 mL)
6. washthe organic layer was washed with aqueous NH4Cl (sat., 2×100 mL)
7. extractionextracted with ethyl acetate (2×150 mL)
8. washThe combined organic extracts were washed with brine (30 mL)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by silica gel column chromatography with ethyl acetate

ORD record

ord-200c2cabca2b41748a97dc011785cf27

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2