Hydrochloric Acid → HCID 15007057, compound

HRID 1613933Notes

Reaction equation

HRID 1613933 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]=[CH:26][CH:27]=2)[N:22]=1)=[O:20].Cl>CCCCCC.O1CCCC1.O>[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]=[CH:26][CH:27]=2)[N:22]=1)/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 123701-OctyneHCID 15007049HCID 15007049, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15007057HCID 15007057, compoundYield 398.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
50 °C

Procedure

13.9 ml of an n-hexane solution of 13.9 mmols of diisobutylaluminium hydride was added to a solution of 1.68 g (1.53 mmols) of 1-octyne in 20 ml of n-hexane in an atmosphere of nitrogen at 0° C. and stirred at 50° C. for 2 hours. After removal of the solvent by distillation under reduced pressure, 20 ml of tetrahydrofuran was added, followed by further addition of a solution, in 15 ml of tetrahydrofuran, of 2.66 g (11.6 mmols) of 2-formyl-3-methyl 4-acetoxyquinoline at -78° C. The reaction temperature was raised from -78° C. to room temperature and the reaction solution was stirred at room temperature for 15 minutes. The solution was added to a solution of 15 ml of 1N hydrochloric acid and 100 ml of water and filtered through Celite, followed by extraction with ethyl acetate, washing with water and then with a saturated sodium chloride aqueous solution, and drying with sodium 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=15:1) to obtain 2.08 g (yield 52%) of 2-(trans-1-hydroxy-2-nonenyl)-3-methyl-4-acetoxyquinoline.

Workup

  1. customAfter removal of the solvent
  2. distillationby distillation under reduced pressure, 20 ml of tetrahydrofuran
  3. additionwas added
  4. temperatureThe reaction temperature was raised from -78° C. to room temperature
  5. stirringthe reaction solution was stirred at room temperature for 15 minutes
  6. filtrationfiltered through Celite
  7. extractionfollowed by extraction with ethyl acetate
  8. washwashing with water
  9. dry with materialwith a saturated sodium chloride aqueous solution, and drying with sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe resultant residue was purified by silica gel column chromatography (solvent: n-hexane : ethyl acetate=15:1)

Sources & evidence

ORD record
ord-0ccf8a826b0a44b1834c00e088512605
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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