Sodium Iodide → HCID 14434680, compound

HRID 259771Notes

Reaction equation

HRID 259771 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:20][CH2:21][OH:22]>CN(C)C=O.C(OCC)(=O)C>[OH:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 84873-HydroxyacetophenoneHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 14434680HCID 14434680, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3'-Hydroxyacetophenone (5.0 g, 37 mmol), potassium carbonate (6.1 g, 44 mmol), sodium iodide (0.28 g, 1.8 mmol), and 2-bromoethanol (2.6 mL, 37 mmol) were stirred in N,N-dimethylformamide (DMF) for 20 h at room temperature, then for 4 days at 70°-80° C. The reaction mixture was diluted with ethyl acetate (EtOAc) and extracted several times with water, then dried over magnesium sulfate (MgSO4), and concentrated in vacuo. Chromatography on silica gel, eluting with 30% to 50% EtOAc in hexanes, after solvent removal, gave a viscous oil (2.1 g). 1H-NMR(300 MHz, CDCl3): 7.56(d, 1H, J=8 Hz), 7.51(s, 1H), 7.39(t, 1H, J=8 Hz), 7.14(d, 1H, J=8 Hz), 4.14 (m, 2H), 3.99 (m, 2H), 2.60 (s, 3H), 2.09 (br, 1H).

Workup

  1. extractionextracted several times with water
  2. dry with materialdried over magnesium sulfate (MgSO4)
  3. concentrationconcentrated in vacuo
  4. washChromatography on silica gel, eluting with 30% to 50% EtOAc in hexanes
  5. customafter solvent removal

Sources & evidence

ORD record
ord-24a5db75ec5a4a199dfe272065f07a65
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Reaction notes

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