Hexane → HCID 15007056, compound

HRID 1613932Notes

Reaction equation

HRID 1613932 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]=[CH:27][CH:28]=2)[N:23]=1)=[O:21]>O1CCCC1.O>[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]=[CH:27][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 15007049HCID 15007049, compoundHCID 178418339Butyllithium

Product 1

HCID 15007056HCID 15007056, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4.9 ml of a hexane solution of 8.00 mmols of n-butyl lithium was added to a solution of 968 mg (8.80 mmols) of 1-octyne in 10 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 1.83 g (8.00 mmols) of 2-formyl-3-methyl-4-acetoxyquinoline was added, following by heating gradually to room temperature and stirring at room temperature for 1 hour. The reaction solution was poured into 100 ml of water, extracted with ethyl acetate and dried with sodium sulfate. The solvent was distilled off under the reduced pressure and resultant residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane ethyl acetate=2:1) to obtain 1.50 g (yield 55%) of 2-(1 hydroxy-2-nonynyl)-3-methyl-4-acetoxyquinoline.

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 the reduced pressure and resultant residue
  6. customwas purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane ethyl acetate=2:1)

Sources & evidence

ORD record
ord-e469771c2be84e2db6877eda0920a833
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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