Potassium Iodide → Ethyl 4-[6-acetyl-3-[2-(4-acetyl-3-hydroxy-2-propylphenylthio)-ethoxy]-2-propylphenoxy]butyrate

HRID 488690Notes

Reaction equation

HRID 488690 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]([O:22][CH2:23][CH2:24]Cl)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH:26][C:27]1[C:32]([CH2:33][CH2:34][CH3:35])=[C:31]([SH:36])[CH:30]=[CH:29][C:28]=1[C:37](=[O:39])[CH3:38].[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]([O:22][CH2:23][CH2:24][S:36][C:31]2[CH:30]=[CH:29][C:28]([C:37](=[O:39])[CH3:38])=[C:27]([OH:26])[C:32]=2[CH2:33][CH2:34][CH3:35])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneHCID 15712390Ethyl 4-[6-acetyl-3-(2-chloroethoxy)-2-propylphenoxy]butyrate

Product 1

HCID 15712393Ethyl 4-[6-acetyl-3-[2-(4-acetyl-3-hydroxy-2-propylphenylthio)-ethoxy]-2-propylphenoxy]butyrateYield 82.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 4-[6-acetyl-3-(2-chloroethoxy)-2-propylphenoxy]butyrate (0.60 g), (2-hydroxy-4-mercapto-3-propylphenyl)ethanone (0.51 g), potassium iodide (0.1 g) and potassium carbonate (0.65 g) in acetone (40 ml) was heated and refluxed with stirring for 19 hours. After cooled, inorganic materials were separated by filtration and the filtrate was concentrated. The resultant residue was separated and purified through silica gel column chromatography (eluting with benzene:ethyl acetate=15:1, then 9:1) to give the title compound (0.73 g, 82.8%) as brown oil.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed
  3. temperatureAfter cooled
  4. custominorganic materials were separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe resultant residue was separated
  7. custompurified through silica gel column chromatography (
  8. washeluting with benzene

Sources & evidence

ORD record
ord-2391c019b6244bd3b15092931190dbb3
Source dataset
uspto-grants-2005_12
Patent number
USRE038921E1

Reaction notes

Loading…