Potassium Carbonate → 1-Ethynyl-3-methanesulfonylbenzene
Reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]#[C:12][Si](C)(C)C)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+]>CO>[C:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=1)#[CH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The TMS-acetylene 1.58 g (626 μmol) was treated with 1.02 g of potassium carbonate and 10.0 mL of methanol. The resulting suspension was stirred at room temperature for 3 h then was concentrated to remove methanol. The residue was washed into a separatory funnel with ethyl acetate and water. The ethyl acetate was separated, washed with ammonium chloride, brine, was dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel flash chromatography (Jones Flashmaster, 50 g Silica gel, gradient elution from 100% hexanes to 40% ethyl acetate over 30 minutes). Appropriate fractions were combined and concentrated in vacuo affording 1-Ethynyl-3-methanesulfonyl-benzene as a cream colored solid, yield: 977 mg (86.6%). 1H NMR (CDCl3): δ 8.07 (s, 1H), 7.92 (d, J=8 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.55 (t, J=8 Hz, 1H), 3.22 (s, 1H), 3.06 (s, 3H).