Potassium Carbonate → Methyl 4-ethynylbenzoate

HRID 76141

Reaction equation

HRID 76141 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 640161Methyl 4-trimethylsilylethynylbenzoate

Product 1

HCID 640163Methyl 4-ethynylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

18.1 g (77.9 mmol) 4-trimethylsilanylethynyl-benzoic acid methyl ester are added to 400 mL MeOH, cooled down to 0° C. and charged with 3.24 g (23.4 mmol) K2CO3. The reaction mixture is stirred for 3 h, then the solvent is removed in vacuo and the resulting residue is purified by column chromatography (silica gel, hexane/TBME 10/1).

Workup

  1. customthe solvent is removed in vacuo
  2. customthe resulting residue is purified by column chromatography (silica gel, hexane/TBME 10/1)

Sources & evidence

ORD record
ord-de8bb91a8f924b978552978698209a98
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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