Chlorotrimethylsilane → Methyl 2-(2-methylquinolin-8-yl)acetate

HRID 338903Notes

Reaction equation

HRID 338903 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl[Si](C)(C)[CH3:18]>CO>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH2:12][C:13]([O:15][CH3:18])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 70984126HCID 70984126, compound

Product 1

HCID 70984092Methyl 2-(2-methylquinolin-8-yl)acetateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-methylquinolin-8-yl)acetic acid (1.45 g, 7.21 mmol) in dry MeOH (100 mL) was added chlorotrimethylsilane (1.82 mL, 14.4 mmol) dropwise at 0° C. After addition, the reaction mixture was stirred at reflux for 2 hours. After cooling to ambient temperature, the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate (20 mL). 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 methyl 2-(2-methylquinolin-8-yl)acetate (1.35 g, 87.0%) as an oil.

Workup

  1. additionAfter addition
  2. temperatureat reflux for 2 hours
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate (20 mL)
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-02cb02e808b2400fbda5e3ac2bee9edd
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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