Ethyl iodoacetate → HCID 21250173, compound

HRID 1531745Notes

Reaction equation

HRID 1531745 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-chlorophenyl)-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 evaporated down. The residue is chromatographed on silica gel, eluting first with petroleum ether and later with petroleum ether/ethyl acetate (8:2 and 1:1). The desired fractions are combined and evaporated down.

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. customevaporated down
  7. customThe residue is chromatographed on silica gel
  8. washeluting first with petroleum ether and later with petroleum ether/ethyl acetate (8:2 and 1:1)
  9. customevaporated down

Sources & evidence

ORD record
ord-4bb78b0b5fd34136a622ba10d64bf834
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

Loading…