Hexane → 2-(1-Hydroxy-2-nonynyl)-3-methyl-4-acetoxy-6-fluoroquinoline

HRID 1613938Notes

Reaction equation

HRID 1613938 reaction equation
CCCCCC.C([Li])CCC.[CH:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH:20]([C:22]1[C:31]([CH3:32])=[C:30]([O:33][C:34](=[O:36])[CH3:35])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:37])[CH:28]=2)[N:23]=1)=[O:21]>O.O1CCCC1>[OH:21][CH:20]([C:22]1[C:31]([CH3:32])=[C:30]([O:33][C:34](=[O:36])[CH3:35])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:37])[CH:28]=2)[N:23]=1)[C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 8058HexaneHCID 123701-OctyneHCID 150070582-Formyl-3-methyl-4-acetoxy-6-fluoroquinolineHCID 178418339Butyllithium

Product 1

HCID 150070622-(1-Hydroxy-2-nonynyl)-3-methyl-4-acetoxy-6-fluoroquinolineYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.32 ml of a hexane solution of 2.16 mmols of n-butyl lithium was added to a solution of 238 mg (2.16 mmols) of 1-octyne and 5 ml of tetrahydrofuran in an atmosphere of nitrogen at 0° C. and stirred at the same temperature for 15 minutes. The reaction solution was cooled to -78° C. to which a solution of 10 ml of tetrahydrofuran of 445 mg (1.80 mmols) of 2-formyl-3-methyl-4-acetoxy-6-fluoroquinoline was added, followed by heating gradually to room temperature and stirring at room temperature for 1 hour. The reaction solution was poured into 50 ml of water, extracted with ethyl acetate and dried with sodium sulfate. The solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (Wako gel C-200) (solvent: n-hexane ethyl acetate=5:1) to obtain 349 mg (yield 54 %) of 2-(1-hydroxy-2-nonynyl)-3-methyl-4-actoxy- 6-fluoroquinoline.

Workup

  1. additionwas added
  2. stirringstirring at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (Wako gel C-200) (solvent: n-hexane ethyl acetate=5:1)

Sources & evidence

ORD record
ord-f35abb680cb5404a9e526bc15e310c20
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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