Hydrochloric Acid → HCID 15007061, compound

HRID 1613936Notes

Reaction equation

HRID 1613936 reaction equation
C([Li])(C)(C)C.I/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CN(P(N(C)C)N(C)C)C.I[CH2:26][C:27]1[C:36]([CH3:37])=[C:35]([O:38][C:39](=[O:41])[CH3:40])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([F:42])[CH:33]=2)[N:28]=1.Cl>[Cu](I)I.O.O1CCCC1.CCOCC.CCCCC>[CH2:26]([C:27]1[C:36]([CH3:37])=[C:35]([O:38][C:39](=[O:41])[CH3:40])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([F:42])[CH:33]=2)[N:28]=1)/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 15355Hexamethylphosphorous triamideHCID 11118103(1E)-1-Iodo-1-octeneHCID 15007060HCID 15007060, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 15007061HCID 15007061, compoundYield 20%

Reagents, catalysts & solvents 5

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

Conditions

Temperature
-35 °C

Procedure

5.99 ml of a pentane solution of 9.34 mmols of t-butyl lithium was added to 1.11 g (4.67 mmols) of trans-1-iodo-1-octene, 15 ml ether solution in an atmosphere of argon at -78° C. and stirred at the same temperature for 2 hours. 400 mg (2.10 mmols) of copper iodide was added to the reaction solution, after which it was heated up to -35° C. and stirred at the same temperature for 45 minutes. 941 mg (5.25 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 628 mg (1.75 mmols) of 2-iodomethyl-3-methyl-4 acetoxy-6-fluoroquinoline was added, followed by stirring at the same temperature for 30 minutes. The reaction solution was added to a solution of 2 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 anhydrous sodium sulfate. The solvent was distilled off under the reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane : ethyl acetate=15:1) to obtain 120 mg (yield 20 %) of 2-(trans-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline.

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 anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under the reduced pressure
  9. customthe residue was purified by silica gel column chromatography (solvent: n-hexane : ethyl acetate=15:1)

Sources & evidence

ORD record
ord-6014a90e90424262b61daffbbe89033b
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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