Water → 2-(trans-1-Hydroxy-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline

HRID 1613940Notes

Reaction equation

HRID 1613940 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH:19]([C:21]1[C:30]([CH3:31])=[C:29]([O:32][C:33](=[O:35])[CH3:34])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:36])[CH:27]=2)[N:22]=1)=[O:20].O>CCCCCC.O1CCCC1>[OH:20][CH:19]([C:21]1[C:30]([CH3:31])=[C:29]([O:32][C:33](=[O:35])[CH3:34])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:36])[CH:27]=2)[N:22]=1)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 123701-OctyneHCID 150070582-Formyl-3-methyl-4-acetoxy-6-fluoroquinolineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 150070632-(trans-1-Hydroxy-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinolineYield 58%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
50 °C

Procedure

10.8 ml of an n-hexane solution of 10.8 mmols of diisobutylaluminium hydride was added to a solution of 1.31 g (11.9 mmols) of 1-octyne in 20 ml of n-hexane in an atmosphere of nitrogen and stirred at 50° C. for 2 hours. The reaction solution was cooled to -78° C., to which a solution of 2.22 ml (9.00 mmols) of 2-formyl-3-methyl-4-acetoxy-6-fluoroquinoline in 30 ml of tetrahydrofuran was added. The reaction temperature was raised from -78° C. to room temperature and the reaction solution was stirred at room temperature for 30 minutes. The reaction solution was added to 100 ml of water and filtered through Celite, followed by extraction with ethyl acetate, washing with water and a saturated sodium chloride aqueous solution, and drying with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (solvent: n-hexane ethyl acetate=8:1) to obtain 1.86 g (yield 58 %) of 2-(trans-1-hydroxy-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline.

Workup

  1. additionwas added
  2. temperatureThe reaction temperature was raised from -78° C. to room temperature
  3. stirringthe reaction solution was stirred at room temperature for 30 minutes
  4. filtrationfiltered through Celite
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with water
  7. dry with materiala saturated sodium chloride aqueous solution, and drying with anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resultant residue was purified by silica gel column chromatography (solvent: n-hexane ethyl acetate=8:1)

Sources & evidence

ORD record
ord-1bd42fd8b16342e49617b1f436503db6
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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