Hydrochloric Acid → HCID 58903196, compound

HRID 273421Notes

Reaction equation

HRID 273421 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[C:26]([F:37])[CH:25]=3)[CH:15]=2)=[C:9]([CH3:38])[CH:8]=1)[CH3:2].CO.[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[C:26]([F:37])[CH:25]=3)[CH:15]=2)=[C:9]([CH3:38])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58903189HCID 58903189, compound

Product 1

HCID 58903196HCID 58903196, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 3-(4-{[4′-(2-ethoxyethoxy)-6-methoxy-2′,6′-dimethylbiphenyl-3-yl]methoxy}-2-fluorophenyl)propanoate (0.45 g, 0.86 mmol), methanol (4.5 mL) and tetrahydrofuran (9 mL) was added 1 N aqueous sodium hydroxide solution (1.7 mL) at room temperature with stirring and the mixture was stirred at the same temperature for 2 hrs. The reaction mixture was neutralized with 1 N hydrochloric acid and concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-hexane/ethyl acetate=1/2) to give the title compound (85 mg, yield 20%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hrs
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-cd0d92ef7244415fa7786c605f478ea0
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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