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

HRID 704117Notes

Reaction equation

HRID 704117 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH:11]([CH2:15][CH3:16])C([O-])=O)=[C:8]([CH2:17][CH2:18][CH3:19])[C:7]([O:20][CH2:21][CH2:22]Cl)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH:24][C:25]1[C:30]([CH2:31][CH2:32][CH3:33])=[C:29]([SH:34])[CH:28]=[CH:27][C:26]=1[C:35](=[O:37])[CH3:36].[I-].[K+].[C:40](=[O:43])([O-])[O-:41].[K+].[K+].[CH3:46][C:47](C)=O>>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:15][CH2:16][C:40]([O:41][CH2:46][CH3:47])=[O:43])=[C:8]([CH2:17][CH2:18][CH3:19])[C:7]([O:20][CH2:21][CH2:22][S:34][C:29]2[CH:28]=[CH:27][C:26]([C:35](=[O:37])[CH3:36])=[C:25]([OH:24])[C:30]=2[CH2:31][CH2:32][CH3:33])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 180AcetoneHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneHCID 867445246-Acetyl-3-(2-chloroethoxy)-2-propylphenoxybutyrate

Product 1

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

Procedure

A mixture of ethyl 4-(6-acetyl-3-(2-chloroethoxy)-2-propylphenoxybutyrate (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-a520185c90c94a4cb5b23548e6a952af
Source dataset
uspto-grants-1991_01
Patent number
US04985585

Reaction notes

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