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

HRID 488689
Notes
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Reaction equation

HRID 488689 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]([OH:22])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][S:35][C:36]1[CH:41]=[CH:40][C:39]([C:42](=[O:44])[CH3:43])=[C:38]([OH:45])[C:37]=1[CH2:46][CH2:47][CH3:48]>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][CH2:32][CH2:33][CH2:34][S:35][C:36]2[CH:41]=[CH:40][C:39]([C:42](=[O:44])[CH3:43])=[C:38]([OH:45])[C:37]=2[CH2:46][CH2:47][CH3:48])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 15623024Ethyl 4-(6-acetyl-3-hydroxy-2-propylphenoxy)butanoateHCID 157123831-{4-[(3-Bromopropyl)sulfanyl]-2-hydroxy-3-propylphenyl}ethan-1-one

Product 1

HCID 15712389Ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyrate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirring mixture of ethyl 4-(6-acetyl-3-hydroxy-2-propylphenoxy)butyrate (1.6 g), potassium iodide (0.5 g) and potassium carbonate (1.45 g) in acetone (30 ml) was added a solution of [4-(3-bromopropylthio)-2-hydroxy-3-propylphenyl]ethanone (1.9 g) in acetone (10 ml) dropwise with heating to reflux. After heating and refluxing with stirring for six hours, inorganic materials were separated by filtration and the filtrate was concentrated. The residue was separated and purified through silica-gel column chromatography (eluting with benzene:ethyl acetate=9:1) to give the title compound as crude crystals (2.1 g, 72.4%). This crystal was recrystallized from ethanol to colorless crystals, mp 65-66° C.

Workup

  1. temperaturewith heating to reflux
  2. temperatureAfter heating
  3. temperaturerefluxing
  4. custominorganic materials were separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was separated
  7. custompurified through silica-gel column chromatography (eluting with benzene:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-7cdbbebc57884419a3d42e2793b6ddc7
Source dataset
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE038921E1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes