Tetrabutylammonium Fluoride → 1-Ethynyl-4-(methoxymethoxy)-2-methylbenzene
Reaction equation
C([Si](CC)(CC)[C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][O:14][CH3:15])=[CH:8][C:7]=1[CH3:16])C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][O:14][CH3:15])=[CH:8][C:7]=1[CH3:16])#[CH:4]Participants
3
Procedure
To a solution of triethyl((4-(methoxymethoxy)-2-methylphenyl)ethynyl)silane (1.0 equiv.) at 0° C. was slowly added tetrabutylammonium fluoride (1M solution in THF, 0.20 equiv.). At this point, the ice-bath was removed and the reaction mixture was allowed to stir at room temperature for 45 minutes. The reaction mixture was then passed through a pad of silica (packed with hexane) and eluted with 20% EtOAc in Hexanes to remove insoluble salts. The crude product was then purified by Combiflash using 0-10% EtOAc in Hexanes to give 1-ethynyl-4-(methoxymethoxy)-2-methylbenzene (8) as a slightly brown liquid.
Workup
- customat 0° C.