18-Crown-6 → HCID 54431059, compound

HRID 263797Notes

Reaction equation

HRID 263797 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11]Cl)[CH3:2].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][N:18]1[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]2[C:14]1=[O:24])[CH3:2]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 14913912HCID 14913912, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 54431059HCID 54431059, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 10.5 g (50 mmol) of 2-[2-(chloroethoxy)-ethoxy]-acetic acid ethyl ester (Chemical Abstracts-Registry No. 82227-25-6) in 100 ml of DMF is reacted with 9.25 g (50 mmol) of potassium phthalimide (Fluka, Buchs, Switzerland) and 50 mg of 18-crown-6 ether (1,4,7,10,13,16-hexaoxacyclooctadecane, Fluka, Buchs, Switzerland) and the mixture is stirred for 2.5 h at 100° C. The reaction mixture is cooled and then concentrated under reduced pressure. The residue is taken up in ether and washed twice in each case with water and brine. After drying and concentrating, the title compound is obtained by column chromatography (SiO2, ethyl acetate/hexane: 1/1); TLC Rf (ethyl acetate/hexane: 4/1)=0.45;

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated under reduced pressure
  3. washwashed twice in each case with water and brine
  4. customAfter drying
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-47f02161a65141be9954bd8107e6a242
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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