Ethyl Acetate → 2-(4-Ethynyl-2-methylphenoxy)ethanol

Reaction equation

CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][C:20]1[CH:29]=[C:28]([C:30]#[C:31][Si](C)(C)C)[CH:27]=[CH:26][C:21]=1[O:22][CH2:23][CH2:24][OH:25].CCOC(C)=O>C1COCC1>[C:30]([C:28]1[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24][OH:25])=[C:20]([CH3:19])[CH:29]=1)#[CH:31]

Participants

Procedure

20.8 g (74.4 mmol) of TBAF was added at RT to a solution of 16.8 g (67.6 mmol) of 2-(2-methyl-4-trimethylsilanylethynylphenoxy)ethanol in 500 mL of THF and the mixture was stirred for 3 hours at RT. The reaction mixture was evaporated down in vacuo and the residue dissolved in EtOAc. The organic phase was washed with water and saturated aqueous NaCl solution, dried over sodium sulfate, and evaporated down in vacuo. The crude product was used in the next reaction step without further purification. Yield: 12.0 g (quant. yield); C11H12O2 (M=176.212); calc.: molpeak (M)+: 176; found: molpeak (M)+: 176; Rf value: 0.24 (silica gel, cyc/EtOAc 2:1).