Lithium hydroxide, monohydrate → HCID 58083453, compound

HRID 2404327Notes

Reaction equation

HRID 2404327 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([O:15]C)=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:26])([F:25])[F:24]>C1COCC1.CO.O>[CH3:4][O:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:24])([F:25])[F:26]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66718285HCID 66718285, compound

Product 1

HCID 58083453HCID 58083453, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (2.29 g, 54.7 mmol) was added into a solution of methyl 2-(methoxymethyl)-2′-(trifluoromethyl)biphenyl-4-carboxylate (8.0 g, 27.3 mmol) in THF (100 mL), MeOH (30 mL) and water (30 mL). The resulting mixture was stirred at RT for 12 hours, and then the reaction mixture was concentrated under vacuum. The remaining aqueous layer was acidified with a concentrated aqueous solution of HCl and extracted with EtOAc. Then the organic layer was washed with water and brine, and then dried (Na2SO4) and concentrated under vacuum. The resulting solid was suspended in Et2O (30 mL), filtered and dried under vacuum to afford of the title compound as a pale yellow solid (6.2 g, 74%). LC/MS (Method B): 309.0 (M−H)−. 1H NMR (DMSO-d6, 400 MHz) δ 13.08 (1H, s), 8.06 (1H, s), 7.87 (2H, m), 7.73 (1H, m), 7.65 (1H, m), 7.35 (1H, d, J=7.5 Hz), 7.27 (1H, d, J=7.9 Hz), 4.11-4.03 (2H, m), 3.15 (3H, s).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. extractionextracted with EtOAc
  3. washThen the organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5dac48cc59094f66a9bd5f6d21d721f6
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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