Potassium Iodide → HCID 86583975, compound

HRID 1270054Notes

Reaction equation

HRID 1270054 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:13]([O:15][C:16](=[O:29])[C@@H:17]([O:26][CH2:27][CH3:28])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH3:14].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.O>[CH2:13]([O:15][C:16](=[O:29])[C@@H:17]([O:26][CH2:27][CH3:28])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:2]/[CH:3]=[CH:4]/[C:5]#[C:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:23][CH:24]=1)[CH3:14]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 546319740316-56-1HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 86583975HCID 86583975, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of (E)-(5-chloro-pent-3-en-1-ynyl)-benzene (177 mg, 1.0 mmol) and (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (238 mg, 1.0 mmol) in acetone (15 mL) was added potassium carbonate (700 mg, 5.0 mmol) and potassium iodide (17 mg, 0.1 mmol). The mixture was heated to reflux over night with stirring. Water was added and the product extracted with tert-butyl methyl ether (×3) The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo, to give the title compound as a crude product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux over night
  3. extractionthe product extracted with tert-butyl methyl ether (×3) The combined organic phases
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d796ea704a19466483e27b0f5290b75b
Source dataset
uspto-grants-2007_04
Patent number
US07202213B2

Reaction notes

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