Potassium Iodide → HCID 15623023, compound

HRID 1493725Notes

Reaction equation

HRID 1493725 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=1[CH2:19][CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C)C=O>[C:15]([C:12]1[C:11]([O:18][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:10]([CH2:19][CH2:20][CH3:21])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 2801568HCID 2801568, compound

Product 1

HCID 15623023HCID 15623023, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4'-benzyloxy-2'-hydroxy-3'-propylacetophenone (3.0 g), anhydrous potassium carbonate (2.9 g), potassium iodide (0.5 g) in N,N-dimethylformamide (40 ml) was stirred at 100° C. To this mixture was added ethyl 4-bromobutyrate (3.1 g) dropwise under stirring and the mixture was stirred for 8 hours. This mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography, eluting with benzene-ethyl acetate (20:1), to give the title compound (2.2 g, 52.3%) as brown oil.

Workup

  1. stirringunder stirring
  2. stirringthe mixture was stirred for 8 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography
  8. washeluting with benzene-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-32d00a1359ce4c879bca3e8eda2d2de9
Source dataset
uspto-grants-1991_06
Patent number
US05023364

Reaction notes

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