HCID 69306558, compound → HCID 69308438, compound

HRID 1393864Notes

Reaction equation

HRID 1393864 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([O:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>CO.O1CCCC1.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([CH:14]([O:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[C:15]([OH:17])=[O:16])=[CH:12][CH:13]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 1

HCID 69306558HCID 69306558, compound

Product 1

HCID 69308438HCID 69308438, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 2-{4-[(4-fluorobenzyl)oxy]phenyl}-2-[(2-methoxyethoxy)methoxy]acetate (0.421 g, 1.11 mmol) was dissolved in a mixture of methanol (6 ml) and tetrahydrofuran (6 ml), and 1N sodium hydroxide (3 ml) was added thereto. After being stirred for 1 hour at room temperature, the reaction mixture was neutralized and then extracted with ethyl acetate. The organic layer dried over MgSO4, and then the solvent was evaporated out. The obtained residue was purified by silica gel column chromatography (50% ethyl acetate/hexane), to give 2-{4-[(4-fluorobenzyl)oxy]phenyl}-2-[(2-methoxyethoxy)methoxy]acetic acid (0.156 g, 39%).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer dried over MgSO4
  4. customthe solvent was evaporated out
  5. customThe obtained residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ddf135d6b1114afda07a0897005ece08
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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