HCID 66906418, compound → HCID 66906306, compound

HRID 1690467Notes

Reaction equation

HRID 1690467 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:18]=3[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7]>[OH-].[Na+]>[F:25][C:24]1[C:18]2[CH:17]=[C:16]([CH2:15][O:14][C:10]3[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:26])=[O:2])[C:5]=3[C:6]([OH:8])=[O:7])[S:20][C:19]=2[CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 66906418HCID 66906418, compound

Product 1

HCID 66906306HCID 66906306, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(4-fluoro-benzo[b]thiophen-2-ylmethoxy)-phthalic acid dimethyl ester (1.5 g, 4.0 mmol) in reagent alcohol (120 mL) and 3 N sodium hydroxide (60 mL) was refluxed for two hours. The solution was evaporated and the residue was dissolved in water (100 mL) and washed with methylene chloride (3×100 mL) then acidified to pH around 4. The resulting mixture was extracted with ethyl acetate (2×100 mL) and the combined organic layers was washed with water (2×100 mL), dried and concentrated to give 3-(4-fluoro-benzo[b]thiophen-2-ylmethoxy)-phthalic acid as an off-white solid (1.2 g, 84% yield). The product was used in the next step without further purification.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in water (100 mL)
  3. washwashed with methylene chloride (3×100 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  5. washthe combined organic layers was washed with water (2×100 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5453f10e2faf4a57a32fb32e99253585
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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