Hydrochloric Acid → HCID 54364423, compound

HRID 1740600Notes

Reaction equation

HRID 1740600 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:18][C:19]([O:21]C)=[O:20].O.O[Li].O.Cl>C1COCC1>[F:24][C:2]([F:1])([F:23])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:18][C:19]([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 53978644HCID 53978644, compound

Product 1

HCID 54364423HCID 54364423, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(2,2,2-trifluoroethoxy)-4-(2-pyridyloxy)phenylacetate (0.45 g, 1.3 mmol) from Step 3 above in THF (4 mL) and water (1 mL) was added LiOH·H2O (0.065 g, 1.5 mmol). The mixture was stirred at ambient temperature for 14 h. The solution was adjusted to pH 3 by the addition of 5 N aqueous HCl and the solvents were removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient elution of 0-20% MeOH:CH2Cl2 to give 2-(2,2,2-trifluoroethoxy)-4-(2-pyridyloxy)-phenylacetic acid as a gum (HPLC retention time=5.4 min (method A)).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was purified by pressurized silica gel column chromatography
  3. washa gradient elution of 0-20% MeOH

Sources & evidence

ORD record
ord-c98059e102da4361bec658842fb07dcb
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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