Tetrabutylammonium Fluoride → HCID 59523103, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6.0 g (7.06 mmol) of compound 12 in 150 mL of THF at 0° C. was added a solution of 21.2 mL (21.2 mmol) of tetrabutylammonium fluoride (1.0 M in THF) dropwise over 5 minutes. The mixture was stirred for 30 minutes at 0° C. then the ice bath was removed and the mixture was stirred at ambient temperature for 90 minutes. The mixture was treated with 2 mL of water, concentrated in vacuo, and separated by flash chromatography (silica gel, 5.5×35 cm, 1:1 hexane:chloroform to methylene chloride). The resulting solid was recrystallized from hexanes to give 2.98 g (79% yield) of compound 13 as colorless needles. 1H NMR (500 MHz) δ 8.43 (s, 2H), 4.47 (t, 4H, J=6.5 Hz), 1.90-1.20 (m, 40H), 0.90 (t, 6H, J=7.0 Hz).

Provenance & Evidence