Water → 2-[4-(2-Cyclopentyl-2-oxo-ethoxy)-2-fluoro-phenyl]-2-methyl-propionitrile

HRID 1453305Notes

Reaction equation

HRID 1453305 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[C:15]([CH3:19])([CH3:18])[C:16]#[N:17].Cl[CH2:21][C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23].O>CN(C=O)C>[CH:24]1([C:22](=[O:23])[CH2:21][O:14][C:12]2[CH:11]=[CH:10][C:9]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[C:8]([F:7])[CH:13]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124665772-Chloro-1-cyclopentylethanoneHCID 601250122-(2-Fluoro-4-hydroxyphenyl)-2-methylpropanenitrile

Product 1

HCID 601250052-[4-(2-Cyclopentyl-2-oxo-ethoxy)-2-fluoro-phenyl]-2-methyl-propionitrileYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (3.1 g, 22 mmol) was added to a solution of 2-(2-Fluoro-4-hydroxy-phenyl)-2-methyl-propionitrile (1.0 g, 6.0 mmol) and 2-Chloro-1-cyclopentyl-ethanone (3.3 g, 22 mmol) in DMF (20 mL). The mixture was stirred at room temperature for 16 hours. The mixture was poured into water (100 mL) and extracted with EtOAc (2×50 mL). The organics were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (0-15% EtOAc in hexanes) to give the product (1.2 g, 75% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ: 1.57-1.93 (m, 14H), 3.10 (m, 1H), 4.64 (s, 2H), 6.65 (d, J=9.6 Hz, 2H), 7.37 (t, J=8.9 Hz, 1H).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe organics were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (0-15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-94414fc279b64ed48be133090635f4ee
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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