Water → N,N-dibutyl-4-ethynylaniline
Reaction equation
[OH-].[K+].C[Si]([C:7]#[C:8][C:9]1[CH:23]=[CH:22][C:12]([N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)(C)C.O>CO>[C:8]([C:9]1[CH:23]=[CH:22][C:12]([N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)#[CH:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Potassium hydroxide (5 mL, 2 M) was added to a solution of 4-trimethysilylethynyl-N,N-dibutylaniline (3 g, 9.1 mmol) in MeOH (100 mL) with stirring. The solution was stirred at 40° C. for 0.5 h, poured into water (200 mL), extracted with Et2O (3×50 mL), washed with water (50 mL), dried (MgSO4) and the solvent removed under reduced pressure to give the title compound (2.35 g, 100%) as a brown oil.