Water → Ethyl 5-(4-cyanophenoxy)pentanoate

HRID 726438Notes

Reaction equation

HRID 726438 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Br[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 23371391Ethyl 5-(4-cyanophenoxy)pentanoateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Cyanophenol (5.0 g) is dissolved in DMF (40 ml), and thereto are added ethyl 5-bromopentanoate (11.4 g) and potassium carbonate (6.38 g), and the mixture is stirred at room temperature for 24 hours. The reaction mixture is poured into water, and the mixture is extracted three times with ethyl acetate. The organic layer is washed successively with a saturated aqueous sodium hydrogen carbonate solution, water and a saturated brine, and dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (silica gel; 100 g, solvent; hexane/ethyl acetate=5:1 to 5:2). The fractions containing the title compound are concentrated under reduced pressure to give the title compound (9.86 g).

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe organic layer is washed successively with a saturated aqueous sodium hydrogen carbonate solution, water
  3. dry with materiala saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe desiccant is removed by filtration
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (silica gel; 100 g, solvent; hexane/ethyl acetate=5:1 to 5:2)
  7. additionThe fractions containing the title compound
  8. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-d79232fd460c4596a82616a7270c854e
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

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