Tetrabutylammonium Fluoride → 3-Ethynyl-4,5-dimethoxybenzoic acid

HRID 638935Notes

Reaction equation

HRID 638935 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:14]#[C:15][Si](C)(C)C)[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.Cl>[C:14]([C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7])#[CH:15]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 686851233,4-Dimethoxy-5-((trimethylsilyl)ethynyl)benzoic acid

Product 1

HCID 713786443-Ethynyl-4,5-dimethoxybenzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3,4-dimethoxy-5-(trimethylsilanylethynyl)benzoic acid (5.56 g, 20 mmol) in THF (115 mL) at 0° C. was added TBAF (1.0 M solution in THF, 30 mL, 30 mmol). The resulting solution was stirred at 0° C. for 30 min, then the reaction mixture was diluted with 1 N HCl aqueous solution (200 mL), extracted with EtOAc (3×70 mL). The combined organic layer was washed with brine (100 mL), dried over Na2SO4, concentrated in vacuo to give 3-ethynyl-4,5-dimethoxybenzoic acid (4.0 g). The product was used without further purification.

Workup

  1. extractionextracted with EtOAc (3×70 mL)
  2. washThe combined organic layer was washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e3a15b306784b8e962bdaf69d6c2c03
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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