Tetrabutylammonium Fluoride → 2-Phenyl-1,3-dioxolane-2-methanol
Reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:12][CH2:11][CH2:10][O:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:13]1([C:8]2([CH2:7][OH:6])[O:12][CH2:11][CH2:10][O:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyldimethyl-(2-phenyl-[1,3]dioxolan-2-yl-methoxy)silane (5.5 g, 18.7 mmol) in tetrahydrofuran (50 ml) was added tetrabutylammonium fluoride (1M in tetrahydrofuran, 56 ml) at room temperature. The mixture was stirred at room temperature for 12 hours. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=3/1) to give (2-phenyl-[1,3]dioxolan-2-yl)methanol (1.54 g, 8.5 mmol, 45%) as a yellow oil.