Methanol → Methyl 3-ethynyl-5-nitrobenzoate

HRID 541738Notes

Reaction equation

HRID 541738 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]#[C:15][Si](C)(C)C)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2].CO.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:14]([C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[CH:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 57961569Methyl 3-nitro-5-[(trimethylsilyl)ethynyl]benzoate

Product 1

HCID 57962750Methyl 3-ethynyl-5-nitrobenzoateYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-nitro-5-[(trimethylsilyl)ethynyl]benzoate (7.9 g, 28 mmol) was dissolved in THF (90 mL) and methanol (90 mL) and then potassium carbonate (2.0 g, 14 mmol) was added. The resulting solution was stirred at room temperature for 1 hour. The reaction was quenched with 1 N HCl, and the solvent was removed in vacuo. The aqueous residue was extracted with ethyl acetate twice. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated to give a solid. The solid was washed with ether to give the desired product (4 g, 68%). LCMS for C10H8NO4 (M+H)+: m/z=206.0.

Workup

  1. customThe reaction was quenched with 1 N HCl
  2. customthe solvent was removed in vacuo
  3. extractionThe aqueous residue was extracted with ethyl acetate twice
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid
  9. washThe solid was washed with ether

Sources & evidence

ORD record
ord-07e56b5a02964ca1bc539a0a768ee8ca
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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