Lithium hydroxide, monohydrate → HCID 59377707, compound

HRID 1691792Notes

Reaction equation

HRID 1691792 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:9]([F:23])=[CH:8][C:7]=1[Br:24])C.O[Li].O>CO>[Br:24][C:7]1[CH:8]=[C:9]([F:23])[C:10]([O:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:20])([CH3:22])[CH3:21])([CH3:17])[CH3:18])=[CH:11][C:6]=1[CH2:5][C:4]([OH:25])=[O:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59377706HCID 59377706, compound

Product 1

HCID 59377707HCID 59377707, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {2-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-fluoro-phenyl}-acetic acid ethyl ester (0.508 g, 1.16 mmol) in MeOH was added LiOH.H2O (0.036 g, 1.51 mmol). The mixture was stirred at room temperature for two hours, and then solvent was removed under reduced pressure. 2N NaOH was added to the residue, and the mixture was washed with diethyl ether. The aqueous phase was taken to pH 1 with 2N HCl and was extracted with EtOAc. The combined EtOAc extracts were washed with water, brine dried over MgSO4, filtered and concentrated to dryness under reduced pressure to yield {2-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-fluoro-phenyl}-acetic acid (0.352 g, 74%) as a white solid.

Workup

  1. customsolvent was removed under reduced pressure
  2. addition2N NaOH was added to the residue
  3. washthe mixture was washed with diethyl ether
  4. extractionwas extracted with EtOAc
  5. washThe combined EtOAc extracts were washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f779c62c4ebd4d81a8c8ead75cb675b6
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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