Potassium Iodide → HCID 68213438, compound

HRID 1186249Notes

Reaction equation

HRID 1186249 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)[CH2:9][CH2:8]2.Br[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][N:13]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1)[CH:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[CH2:11]1)[CH3:34]

Participants

6

Reactant 4

HCID 4875Potassium Iodide3×HCID 10796Cesium carbonateHCID 84580Ethyl 5-bromovalerateHCID 68213446HCID 68213446, compound

Product 1

HCID 68213438HCID 68213438, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under argon, 13.4 g (41.2 mmol) of the compound from Example 1A were dissolved in 160 ml of acetonitrile, 11.8 ml (15.5 g, 74.1 mmol) of ethyl 5-bromovalerate, 27 g (82.4 mmol) of cesium carbonate and 685 mg (4.1 mmol) of potassium iodide were added and the mixture was stirred under reflux overnight. After addition of a further 550 mg of potassium iodide, the mixture was once more stirred under reflux overnight. Another 2 g of potassium iodide were then added, and the mixture was again stirred under reflux overnight. After cooling, the precipitate was filtered off and the filtrate was concentrated. This residue was then purified chromatographically on 1.2 kg of silica gel using the mobile phase isohexane/ethyl acetate (gradient 10:1→5:1). This gave 10.95 g (59% of theory) of the title compound as a colorless solid.

Workup

  1. temperatureunder reflux overnight
  2. stirringthe mixture was once more stirred
  3. temperatureunder reflux overnight
  4. stirringthe mixture was again stirred
  5. temperatureunder reflux overnight
  6. temperatureAfter cooling
  7. filtrationthe precipitate was filtered off
  8. concentrationthe filtrate was concentrated
  9. customThis residue was then purified chromatographically on 1.2 kg of silica gel using the mobile phase isohexane/ethyl acetate (gradient 10:1→5:1)

Sources & evidence

ORD record
ord-1033199a89c24f179ace13cb9ab5e0c1
Source dataset
uspto-grants-2014_03
Patent number
US08673903B2

Reaction notes

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