Tetrabutylammonium Fluoride → HCID 12017361, compound

Participants

Reaction Steps

(4E,6E)-9-[1,3]Dioxolan-2-yl-7-methyl-nona-4,6-dien-1-ol was synthesized in the following manner. A solution of tert-butyl-(4E,6E)-(9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dienyloxy)-diphenyl-silane (3.35 g, 7.28 mmol) in 75 mL of THF was cooled to 0° C. and treated dropwise with 10 mL of a 1 M solution of TBAF in THF. The reaction mixture was stirred at 0° C. to room temperature for 11 hours, quenched with a saturated NaHCO3 solution, extracted with Et2O, dried (Na2SO4), and concentrated. Purification of the residue by column chromatography on SiO2 (2:1 hexanes-EtOAc) provided 1.44 g (6.38 mmol, 88%) of oily (4E,6E)-9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dien-1-ol: 1H NMR δ6.28 (dd, 1H, J=14.9, 10.9 Hz), 5.84 (d, 1H, J=10.7 Hz), 5.59 (dt, 1H, J=14.4, 7.0 Hz), 4.86 (t, 1H, J=4.7 Hz), 4.00-3.80 (m, 4H), 3.67 (t, 2H, J=6.5Hz) 2.50-2.38 (m, 1H), 2.25-2.10 (m, 4H), 1.80-1.75 (m, 2H), 1.75 (s, 3H), 1.68 (p, 2H, J=6.7 Hz).

Provenance & Evidence