Water → HCID 10295840, compound

HRID 984947Notes

Reaction equation

HRID 984947 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[C:15](/[C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)C.[OH-].[Na+].O>C1COCC1.C(O)C>[Br:28][C:25]1[CH:24]=[CH:23][C:22](/[C:15](/[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:14]/[CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:29])=[O:3])=[CH:7][CH:8]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69793279HCID 69793279, compound

Product 1

HCID 10295840HCID 10295840, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (E)-{4-[3-(4-bromo-phenyl)-3-phenyl-allyloxy]-phenyl}-acetic acid ethyl ester (example 11) (700 mg, 1.6 mmol) in THF (5 m) and ethanol (5 ml) was added 1N, NaOH (5.0 ml) and the reaction mixture was stirred for 1 h at 60° C. for 1 h and at room temperature over night. The reaction mixture was added water and the organic solvent evaporated. 1 N HCl was added to pH ˜1-2 and the product extracted with dichloromethane/isopropanol (19:1). The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The residue was suspended in toluene/petroleum ether (1:1) and 490 mg (70%) of the title compound was isolated by filtration.

Workup

  1. customthe organic solvent evaporated
  2. addition1 N HCl was added to pH ˜1-2
  3. extractionthe product extracted with dichloromethane/isopropanol (19:1)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72041867e2a54f6a9d0fbd459048d28e
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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