Synthesis
GENERAL PROCEDURE: To a 25 mL round-bottomed flask, (2,6-dimethoxyphenyl)ethynyltrimethylsilane (1 mmol) and 5 mL of anhydrous tetrahydrofuran were added under nitrogen protection. Subsequently, tert-butylammonium fluoride (0.5 mmol) in 1 M tetrahydrofuran solution was slowly added to this solution. During the reaction, the colorless solution gradually changed to light to dark brown. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, silica gel (500 mg) was added to the mixture, followed by evaporation of the solvent under reduced pressure to obtain a silica gel plug. This silica plug was loaded on a silica gel column (2 cm × 5 cm) and eluted using hexane solution containing 5% ethyl acetate. The eluate corresponding to the product spot was collected and the solvent was evaporated under reduced pressure to finally obtain the target product 2-alkynyl-1,3-dimethoxybenzene.
References
[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 14, p. 4355 - 4365
[2] Advanced Synthesis and Catalysis, 2010, vol. 352, # 1, p. 201 - 211
[3] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951
