Sodium Hydroxide → [2-(3-Fluoro-4-methoxy-phenyl)-cyclopropyl]-acetic acid

HRID 62899Notes

Reaction equation

HRID 62899 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:12][CH:11]2[CH2:13][CH:14]=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[OH-:16].[Na+]>CCO.O.[N+]([O-])([O-])=O.[Ag+]>[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:12][CH:11]2[CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 20792239HCID 20792239, compound

Product 1

HCID 90118326[2-(3-Fluoro-4-methoxy-phenyl)-cyclopropyl]-acetic acidYield 79.6%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

[2-(3-Fluoro-4-methoxy-phenyl)-cyclopropyl]-acetaldehyde (0.088 g, 0.42 mmol) obtained in Step C was dissolved in EtOH (2 mL). AgNO3(0.143 g, 0.84 mmol) dissolved in water (0.26 mL) and NaOH (0.067 g, 1.69 mmol) dissolved in water (0.26 mL) was added thereto in turn, and the mixture was stirred for 3 hours. After the termination of the reaction, the reactant was filtered by using celite to remove solid material, and 1N HCl aqueous solution was added to adjust the pH of the solution to 2. The organic layer obtained by the extraction with EtOAc was separated, dried with MgSO4, and concentrated under reduced pressure to obtain the title compound (0.075 g, 79%).

Workup

  1. additionwas added
  2. customAfter the termination of the reaction
  3. filtrationthe reactant was filtered
  4. customto remove solid material, and 1N HCl aqueous solution
  5. additionwas added
  6. customThe organic layer obtained by the extraction with EtOAc
  7. customwas separated
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba12f7c9db334e34bcaddd916fc3ddf8
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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