Water → HCID 23136278, compound

HRID 1678607Notes

Reaction equation

HRID 1678607 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([F:17])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1.[CH2:25](I)[CH:26]([CH3:28])[CH3:27].[H-].[Na+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([F:17])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:25][CH:26]([CH3:28])[CH3:27])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 23136431HCID 23136431, compound

Product 1

HCID 23136278HCID 23136278, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-{3,5-difluoro-4-[(3-hydroxybenzyl)oxy]phenyl}propanoate (200 mg, 0.59 mmol) was dissolved in DMF (10 mL), isobutyl iodide (339 μL, 3.0 mmol) and sodium hydride (47 mg, 1.2 mmol) were added thereto, and then the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 80:20) to give the title compound (186 mg, yield 80%) as an oily matter.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-f703bc50b74641278fbd7acc6342d25e
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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