Lithium Hydroxide → HCID 59637288, compound

HRID 1027971Notes

Reaction equation

HRID 1027971 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:15]([F:24])[CH:14]=2)[C:8]([O:10]CC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:15]([F:24])[CH:14]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59637315HCID 59637315, compound

Product 1

HCID 59637288HCID 59637288, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-phenyl-2-(3-fluoro-4-(methylsulfonamido)-phenyl)acetate (16.5 mmol, 5.8 g) was dissolved in a mixture of 32 mL of THF and 16 mL of water, 1.18 g of LiOH (49.5 mmol) were added, and the mixture was heated under reflux over a period of 15 h. To the reaction mixture there were added 15 mL of water and the phases were separated. The aqueous phase was acidified with aq. HCl and extracted with dichloromethane (3×50 mL). The combined organic phases were dried over MgSO4, concentrated, and the residue purified by means of column chromatography (silica gel: 100-200 mesh, eluent: 50% EA in cyclohexane). Yield 3.3 g (61.3%).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux over a period of 15 h
  4. customthe phases were separated
  5. extractionextracted with dichloromethane (3×50 mL)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated
  8. customthe residue purified by means of column chromatography (silica gel: 100-200 mesh, eluent: 50% EA in cyclohexane)

Sources & evidence

ORD record
ord-fd5d539b07f1404b899f8f162e008431
Source dataset
uspto-grants-2014_05
Patent number
US08735426B2

Reaction notes

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