Sodium Hydroxide → HCID 57894201, compound

HRID 1822348Notes

Reaction equation

HRID 1822348 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[CH:14]=2)=[CH:8][C:7]=1[CH3:35].[OH-].[Na+]>CO>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]([CH3:35])[CH:8]=2)=[C:21]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57894121HCID 57894121, compound

Product 1

HCID 57894201HCID 57894201, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-{3-[4-chloro-2-(2-fluoro-phenoxy)-phenoxy]-phenoxy}-2-methyl-phenyl)-propionic acid methyl ester (72 mg, 0.1 mmol) in MeOH (10 mL) is treated with 5N aqueous sodium hydroxide (0.3 mL). The reaction is heated to reflux and stirred for 2 hr. The reaction is cooled to room temperature and quenched with 1N aqueous HCl to pH=4. The aqueous is extracted with diethyl ether. The organic is washed with brine, dried over sodium sulfate and filtered. The solvent is removed to afford about 60 mg (87%) of product. 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calcd for C28H22ClFO5 506, found 524 (M+NH4, 100%).

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux
  3. customquenched with 1N aqueous HCl to pH=4
  4. extractionThe aqueous is extracted with diethyl ether
  5. washThe organic is washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent is removed

Sources & evidence

ORD record
ord-6cb76a072d2140eda854e4e6b9be6fba
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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