Cesium carbonate → HCID 18798689, compound

HRID 356462

Reaction equation

HRID 356462 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:25]([OH:27])[CH3:26]>O1CCOCC1>[OH:27][CH2:25][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:17])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 144161631-(4-Hydroxyphenyl)-3-phenylpropan-1-oneHCID 17859945HCID 17859945, compound

Product 1

HCID 18798689HCID 18798689, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-(4-hydroxy-phenyl)-3-phenyl-propan-1-one from Example K (6.9 g, 30.5 mmol), and cesium carbonate (19.9 g, 61 mmol) was dissolved in dioxane (300 mL). This mixture was heated to reflux for 1 hour then treated with iodoethanol (2.85 mL, 36.5 mmol) and refluxed overnight; the reaction mixture was cooled and concentrated. The product was partitioned between EtOAc and 1N HCl. The organic layer was dried (MgSO4) and concentrated to dryness. Purification by silica gel chromatography, eluting with EtOAc:hexane (30:70 to 50:50) gave the title compound, m.p. 41°-43° C. 1H NMR (CDCl3) δ 1.96 (t, 1 H), 3.02 (t, 2 H), 3.22 (t, 2 H), 3.95 (m, 2 H), 4.10 (m, 2 H), 6.92 (d, 2 H), 7.15-7.28 (m, 5 H), 7.90 (d, 2 H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturerefluxed overnight
  4. temperaturethe reaction mixture was cooled
  5. concentrationconcentrated
  6. customThe product was partitioned between EtOAc and 1N HCl
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated to dryness
  9. customPurification by silica gel chromatography
  10. washeluting with EtOAc:hexane (30:70 to 50:50)

Sources & evidence

ORD record
ord-e69806be19c2469fbfa3e32de57a6628
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Linked notes

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