Potassium Iodide → Methyl 2-acetyl-5-phenylpentanoate

HRID 1368290Notes

Reaction equation

HRID 1368290 reaction equation
[CH3:1][O:2][C:3](=[O:8])/[CH:4]=[C:5](/[O-:7])\[CH3:6].[Na+].[I-].[K+].Br[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN1CCCN(C)C1=O>[CH3:1][O:2][C:3](=[O:8])[CH:4]([C:5](=[O:7])[CH3:6])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 12503(3-Bromopropyl)benzeneHCID 23681258sodium (2E)-4-methoxy4-oxo-2-buten-2-olate

Product 1

HCID 11333780Methyl 2-acetyl-5-phenylpentanoate

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
80 °C

Procedure

85 g (616 mmol) of sodium (2E)-4-methoxy-4-oxo-2-buten-2-olate suspended in 1,3-dimethyltetrahydro-2(1H)-pyrimidone and 3.50 g (21.1 mmol) of potassium iodide are treated dropwise with 129 g (646 mmol) of 1-bromo-3-phenylpropane and the mixture is stirred under reflux at 80° C. for 1 h. The cooled mixture is then added to ice water and extracted with diethyl ether. The ether phase is washed with sodium thiosulphate solution, dried, concentrated and chromatographed. The eluent used is cyclohexane containing an increasing proportion of ethyl acetate.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether phase is washed with sodium thiosulphate solution
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-f1645386bb714d2d9c8a0c8c7f0e3c48
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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