Cesium carbonate → 1-[4-(2-Hydroxy-ethoxy)-phenyl]-3-phenyl-propan-1-one

HRID 1003816Notes

Reaction equation

HRID 1003816 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 178599451-Iodoethanol

Product 1

HCID 187986891-[4-(2-Hydroxy-ethoxy)-phenyl]-3-phenyl-propan-1-one

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-691ad9153d0e420187ca3754d3c1bb48
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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