Potassium Iodide → HCID 54310319, compound

HRID 617599Notes

Reaction equation

HRID 617599 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][CH:8]([NH:18][C:19](=[O:21])[CH3:20])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)(=[O:5])[CH3:4].[CH2:22](Br)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[I-].[K+]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C.CCCCCC.O>[C:3]([O:6][CH2:7][CH:8]([NH:18][C:19](=[O:21])[CH3:20])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:15][CH:16]=1)(=[O:5])[CH3:4]

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 123691-BromoheptaneHCID 24758Sodium hydrideHCID 54406535HCID 54406535, compound

Product 1

HCID 54310319HCID 54310319, compoundYield 42.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a suspension of sodium hydride (0.076 g) in dimethylformamide (1 ml) and tetrahydrofuran (1 ml), under a nitrogen atmosphere, a solution of 2-acetamido-4-(4-hydroxyphenyl)butyl acetate (0.51 g) in dimethylformamide (2 ml) was added and the mixture was stirred at room temperature for 50 minutes. Then, to the solution, heptyl bromide (0.35 g) and catalytic amount of potassium iodide were added and the mixture was stirred at 60° C. for 4 hours and 40 minutes. Then, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with a dilute aqueous sodium hydrogencarbonate solution and a saturated brine, dried over sodium sulfate and the solvent was distilled away under reduced pressure. The residue obtained was subjected to silica gel chromatography (eluent; ethyl acetate-hexane=4:1) to give the subject compound (0.30 g).

Workup

  1. stirringthe mixture was stirred at 60° C. for 4 hours and 40 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a dilute aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated brine, dried over sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe residue obtained

Sources & evidence

ORD record
ord-5558e7dcc86242188a2301f159da778c
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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