1-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]ethanol → 1-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanone

HRID 378378Notes

Reaction equation

HRID 378378 reaction equation
[CH3:1][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([OH:16])[CH3:15])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:3]>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH3:3][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14](=[O:16])[CH3:15])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:1]

Participants

4

Reactant 1

HCID 106089181-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]ethanol

Product 1

HCID 107751501-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanoneYield 62.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

2.1 g of 1-[1-(1-methylethyl)-1,2,3,4-tetrahydro-quinolin-6-yl]ethanol was dissolved in 10 ml of acetone, followed by the addition of 10 g of activated manganese dioxide. The obtained mixture was stirred at room temperature for 16 hours and filtered though Celite to remove the manganese dioxide. The filtrate was concentrated in a vacuum and the obtained residue was purified by silica gel column chromatography (10% ethyl acetate/n-hexane) to give 1.3 g of the title compound as a pale-yellow crystal.

Workup

  1. filtrationfiltered though Celite
  2. customto remove the manganese dioxide
  3. concentrationThe filtrate was concentrated in a vacuum
  4. customthe obtained residue was purified by silica gel column chromatography (10% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-facfacf81e754ceaa2684abefaa29ee2
Source dataset
uspto-grants-2000_02
Patent number
US06030964

Reaction notes

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