Potassium Iodide → HCID 15712403, compound

HRID 488694Notes

Reaction equation

HRID 488694 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([SH:22])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Br[CH2:24][CH2:25][CH2:26][S:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[C:30]([OH:37])[C:29]=1[CH2:38][CH2:39][CH3:40].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([S:22][CH2:24][CH2:25][CH2:26][S:27][C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[C:30]([OH:37])[C:29]=2[CH2:38][CH2:39][CH3:40])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 157123831-{4-[(3-Bromopropyl)sulfanyl]-2-hydroxy-3-propylphenyl}ethan-1-oneHCID 15712395HCID 15712395, compound

Product 1

HCID 15712403HCID 15712403, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 4-(6-acetyl-3-mercapto-2-propylphenoxy)butyrate (2.0 g), (4-(3-bromopropylthio)-2-hydroxy-3-propylphenyl)ethanone (2.0 g), potassium iodide (0.5 g) and potassium carbonate (1.7 g) in acetone (40 ml) was heated with refluxing and stirring for 9 hours. After cooled, inorganic materials were separated by filtration and the filtrate was concentrated. The resultant residue was separated, and was purified through silicagel column chromatography (eluting with benzene:ethyl acetate=9:1) to give the title compound (1.8 g, 50.8%) as yellow oil.

Workup

  1. temperaturewas heated
  2. temperaturewith refluxing
  3. temperatureAfter cooled
  4. custominorganic materials were separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe resultant residue was separated
  7. customwas purified through silicagel column chromatography (eluting with benzene:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-538f87753d964e64a43b659bb941ef8e
Source dataset
uspto-grants-2005_12
Patent number
USRE038921E1

Reaction notes

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