Hydrochloric Acid → HCID 15007055, compound

HRID 1613930Notes

Reaction equation

HRID 1613930 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])C.CN(P(N(C)C)N(C)C)C.I[CH2:17][C:18]1[C:27]([CH3:28])=[C:26]([O:29][C:30](=[O:32])[CH3:31])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.Cl>[Cu](I)I.O.O1CCCC1.CCOCC.CCCCC>[CH2:17]([C:18]1[C:27]([CH3:28])=[C:26]([O:29][C:30](=[O:32])[CH3:31])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1)/[CH:17]=[CH:18]/[CH2:27][CH2:26][CH2:25][CH2:3][CH2:1][CH3:4]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 15355Hexamethylphosphorous triamideHCID 15007054HCID 15007054, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 15007055HCID 15007055, compoundYield 45.3%

Reagents, catalysts & solvents 5

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

10 ml of a pentane solution of 15.6 mmols of t-butyl lithium was added to 15 ml of 1.86 g (7.8 mmols) of trans-1 -iodo-1-octene ether solution in an atmosphere of argon at -78° C. and stirred at the same temperature for 2 hours. The reaction solution was added to 15 ml of an ether solution of 590 mg (3.10 mmols) of copper iodide at -78° C., after which it was heated up to -35° C. and stirred at the same temperature for 45 minutes. 1.79 g (10 mmols) of hexamethylphosphorus triamide was added to the solution and stirred at -35° C. for 10 minutes, to which 10 ml of a tetrahydrofuran solution of 1.02 g (3.00 mmols) of 2-iodomethyl-3-methyl-4-acetoxyquinoline was added, followed by stirring at the same temperature for 30 minutes. The reaction solution was added to a solution of 3 ml of 1N hydrochloric acid and 100 ml of water, followed by filtration through Celite. The resultant filtrate was extracted with chloroform, washed with water and dried with sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=15:1) to obtain 221 mg (yield 23%) of 2-(trans-2-nonenyl)-3-methyl-4-acetoxyquinoline

Workup

  1. stirringstirred at the same temperature for 45 minutes
  2. additionwas added
  3. stirringby stirring at the same temperature for 30 minutes
  4. filtrationfollowed by filtration through Celite
  5. extractionThe resultant filtrate was extracted with chloroform
  6. washwashed with water
  7. dry with materialdried with sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=15:1)

Sources & evidence

ORD record
ord-755b01b6fb264c5e93690eba83fc8289
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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