Tetrabutylammonium Fluoride → HCID 11095065, compound
Reaction equation
[CH3:1][O:2][C@:3]([CH3:16])([CH2:12][CH2:13][CH2:14][CH3:15])[C@@H:4]([OH:11])[C:5]#[C:6][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C@:3]([CH3:16])([CH2:12][CH2:13][CH2:14][CH3:15])[C@@H:4]([OH:11])[C:5]#[CH:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dissolve (3S,4R)-4-methoxy-4-methyl-1-trimethylsilyl-1-octyn-3-ol (90 mg, 0.37 mmol) in tetrahydrofuran (2 mL) and place under an argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (3.7 mL) of a 1M solution in tetrahydrofuran, 3.7 mmol). Stir for 1 hour at room temperature and partition between methylene chloride and water. Separate the organic phase, wash with saturated aqueous sodium chloride and dry (MgSO4). Evaporate the solvent in vacuo and purify by silica gel chromatography (19:1 hexane/ethyl acetate) to give the title compound as a clear thick oil (55 mg, 87%).