Lithium Hydroxide → HCID 66801889, compound

To a stirred solution of (E)-methyl 3-(2-(2,6-dichlorophenyl)thiazol-4-yl)acrylate (6.3 g, 20 mmol) in MeOH (100 mL) and H2O (20 mL) was added lithium hydroxide (1.5 g, 61 mmol). The resulting mixture was stirred for 24 hours and then partially concentrated under reduced pressure. The pH of the residual aqueous mixture was adjusted to 5 by addition of 2N HCl and extracted with EtOAc (3×100 mL). The combined organic extract was washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with a 0-20% gradient of MeOH in DCM to give the desired product as a white solid (5.4 g, 94% yield). LCMS (ESI) m/z: 300.0 [M+H+].

1. concentrationpartially concentrated under reduced pressure
2. additionThe pH of the residual aqueous mixture was adjusted to 5 by addition of 2N HCl
3. extractionextracted with EtOAc (3×100 mL)
4. extractionThe combined organic extract
5. washwas washed with brine (100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography
9. washeluting with a 0-20% gradient of MeOH in DCM

ORD record

ord-c554d967eb314e5db9c6cfb733abc466

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697708B2