Water → 8-(1-Methoxy-2-methylpropan-2-yl)-2-methylquinoline

HRID 338907Notes

Reaction equation

HRID 338907 reaction equation
[CH3:1][C:2]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2)([CH3:5])[CH2:3][OH:4].I[CH3:18].[H-].[Na+].O>CS(C)=O.CCOCC>[CH3:18][O:4][CH2:3][C:2]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2)([CH3:1])[CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 709839442-Methyl-2-(2-methylquinolin-8-yl)propan-1-ol

Product 1

HCID 709834928-(1-Methoxy-2-methylpropan-2-yl)-2-methylquinolineYield 93.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-methyl-2-(2-methylquinolin-8-yl)propan-1-ol (0.43 g, 2.00 mmol) and iodomethane (0.37 mL, 5.99 mmol) in DMSO (10 mL) was added NaH (0.16 g, 3.99 mmol) at ambient temperature and stirred at ambient temperature for 30 minutes. Water (10 mL) and ether (40 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 8-(1-methoxy-2-methylpropan-2-yl)-2-methylquinoline (0.43 g, 93.0%) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b8eb06ee73c644ff80fe07819fc9fddf
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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