Tetrabutylammonium Fluoride → 1-Undecyn-3-ol

Participants

Reaction Steps

To 8.65 g of the crude product from Example 6 was added 40 ml of 1M (n-C4H9)4NF in tetrahydrofuran (THF). The reaction mixture became warm and stirring was continued at room temperature for 1/2 hour. Thereafter, the reaction mixture was poured into brine and extracted 2× with diethyl ether. The combined ether extracts were washed 2× with brine and then dried (MgSO4). Removal of the solvent produced a brown oil. The oil was flash chromatographed on a silica gel column. Gradient elution from 10% diethyl ether in petroleum ether to 20% diethyl ether in petroleum ether produced 6.81g of the titled product as a yellow oil.

Provenance & Evidence