Methyl iodide → 2-[3-(2-Methylhexanoyl) phenoxymethyl]quinoline

HRID 414835Notes

Reaction equation

HRID 414835 reaction equation
[C:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[CH3:28]I>C1COCC1>[CH3:28][CH:2]([CH2:3][CH2:4][CH2:5][CH3:6])[C:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13560729HCID 13560729, compound

Product 1

HCID 143491272-[3-(2-Methylhexanoyl) phenoxymethyl]quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the ketone, 2-(3-hexanoylphenoxymethyl)quinoline (prepared from 3-hexanoylphenol and 2-chloromethyl quinoline)(6 g, 0.018 mol) in dry THF (25 ml) was added slowly to a mildly refluxing suspension of sodium hydride (1.3 g, 0.054 mol) in dry THF (75 ml) containing excess methyl iodide (10.3 g, 0.073 mol) After the addition of the ketone was complete (30 min.), the reaction mixture was refluxed for 4 hours. After cooling the mixture to room temperature, excess NaH was destroyed by adding methanol. All volatiles were removed at the rotary evaporator and the residue was taken up in ethyl acetate. The organic extract was washed with water and brine, and dried over anhydrous magnesium sulfate. Upon removal of all solvent, the mono-methylated eetone (2-[3-(2-methylhexanoyl) phenoxymethyl]quinoline, was obtained as a yellow oil weighing 8 g.

Workup

  1. temperaturea mildly refluxing
  2. custom(30 min.)
  3. temperaturethe reaction mixture was refluxed for 4 hours
  4. customexcess NaH was destroyed
  5. additionby adding methanol
  6. customAll volatiles were removed at the rotary evaporator
  7. extractionThe organic extract
  8. washwas washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customUpon removal of all solvent

Sources & evidence

ORD record
ord-0d554e52cc8348f0acce04e90bb67428
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

Loading…