Hydrochloric Acid → HCID 54361685, compound

HRID 2289337Notes

Reaction equation

HRID 2289337 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:13]=[N:14][CH:15]=[CH:16][CH:17]=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:13]=[N:14][CH:15]=[CH:16][CH:17]=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 54537748HCID 54537748, compound

Product 1

HCID 54361685HCID 54361685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(2,2,2-trifluoroethoxy)-4-(3-pyridyloxy)phenylacetate (0.45 g, 1.3 mmol) from Step 2 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-trifluoro-ethoxy)-4-(3-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-2671cdc358784a1b8c1b124057ddb466
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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