Tetrabutylammonium Fluoride → 3-Methyl-1-nonyn-3-ol

Participants

Reaction Steps

Dissolve 1-trimethylsilyl-3-methyl-1-nonyn-3-ol (1.94 g, 9.13 mmol) in tetrahydrofuran (11 mL) and place under an argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (11 mL of a 1M solution in tetrahydrofuran, 11 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, dry (MgSO4), filter and evaporate the solvent in vacuo to give the title compound.

Provenance & Evidence