Methanol → Methyl 2-(benzamido)-4-ethynylbenzoate

HRID 1673347Notes

Reaction equation

HRID 1673347 reaction equation
C(=O)([O-])[O-].[K+].[K+].CO.[C:9]([NH:17][C:18]1[CH:27]=[C:26]([C:28]#[C:29][Si](C)(C)C)[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[C:9]([NH:17][C:18]1[CH:27]=[C:26]([C:28]#[CH:29])[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 57879451Methyl 2-(benzamido)-4-(2-(trimethylsilyl)ethynyl)benzoate

Product 1

HCID 57879399Methyl 2-(benzamido)-4-ethynylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.68 g of potassium carbonate was added, to a solution of 17 mL of methanol and 17 mL of tetrahydrofuran containing 3.5 g of methyl 2-(benzamido)-4-(2-(trimethylsilyl)ethynyl)benzoate and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to obtain 1.6 g of methyl 2-(benzamido)-4-ethynylbenzoate as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid
  2. additionwere added
  3. custominsoluble were removed by filtration
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with 1.0 mol/L hydrochloric acid
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=8:1]

Sources & evidence

ORD record
ord-f1728e6235e64387931c615d71defd5e
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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