Ethyl iodoacetate → HCID 21250173, compound

HRID 1953283Notes

Reaction equation

HRID 1953283 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].I[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9](=[O:10])[N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 5112377HCID 5112377, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21250173HCID 21250173, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

16.8 g (0.075 mol) of 2-(4-chloro-phenyl)-1-pyrrolidin-1-yl-ethanone are dissolved in 175 ml dimethylsulphoxide and after the addition of 8.9 g (0.08 mol) of potassium tert.butoxide stirred for 15 minutes at ambient temperature. After the addition of 18.1 ml (0.085 mol) of ethyl iodoacetate the reaction mixture is stirred for 45 hours at ambient temperature. The solution is poured onto ice water and extracted with ethyl acetate. The combined organic extracts are washed with sodium chloride solution, dried and concentrated by evaporation. The residue is chromatographed on silica gel, initially eluting with petroleum ether and later with petroleum ether/ethyl acetate (8:2 and 1:1). The desired fractions are combined and concentrated by evaporation.

Workup

  1. stirringis stirred for 45 hours at ambient temperature
  2. additionThe solution is poured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed with sodium chloride solution
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel
  8. washinitially eluting with petroleum ether and later with petroleum ether/ethyl acetate (8:2 and 1:1)
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d51cc2ef5e7842328037e8fa62a4214e
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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