Hydrochloric Acid → HCID 86650600, compound

HRID 1257441Notes

Reaction equation

Br[C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[S:4][C:3]=1[CH3:17].C([Li])CCC.CN(C)[CH:25]=[O:26].Cl>O1CCCC1>[CH3:17][C:3]1[S:4][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)=[CH:6][C:2]=1[CH:25]=[O:26]

Participants

Conditions

Temperature: -78 °C

Procedure

The compound (0.83 g) obtained in Example 129a was dissolved in tetrahydrofuran (15 mL), cooled to −78° C., and n-butyllithium (2.5M hexane solution, 1.24 mL) was added. The mixture was stirred at the same temperature for 1 hr, N,N-dimethylformamide (1.0 mL) was added, the reaction mixture was warmed to room temperature and stirred for 1 hr. 1N Hydrochloric acid (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane/ethyl acetate) to give the title compound (0.45 g) as a solid.

Workup

temperaturethe reaction mixture was warmed to room temperature
stirringstirred for 1 hr
extractionthe mixture was extracted with ethyl acetate
washThe obtained organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-a76b7f138b624bf3bd9a3ebb3793aafe
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461348B2

Reaction notes

Loading…