Sodium Iodide → HCID 86608406, compound

Participants

Reaction Steps

The crude methanesulfonate 4 (3.30 g, 9.8 mmol) was used directly in the following reaction by mixing with a freshly ground mixture of triphenylphosphine (4.08 g, 15.6 mmol) and NaI (7.78 g, 51.9 mmol) in a Kimax tube and sealed under argon. The mixture was then held at 70-74° C. with magnetic stirring for 3 hrs during which time the mixture changed from a molten thick liquid into a glassy solid. The tube was cooled to room temperature and the residue stirred with CH2Cl2 (30 mL). The suspension was then filtered and the filtrate evaporated in vacuo. The residue was dissolved in a minimum amount of CH2Cl2 and triturated with excess ether (250 mL) to precipitate the white solid. The solid was filtered and washed with ether, dried in vacuo to give pure [3-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-propyl]triphenylphosphonium iodide (5) (5.69 g, 90%). 1H NMR δ 7.82-7.65 (15H, m, Ar—H), 3.88, 3.86, 3.74, 3.73 (12H, s, OMe), 3.76-3.88 (2H, m, CH2—P+), 2.98 (2H, t, J=7.0 Hz, CH2—Ar), 2.13 (3H, s, Ar-Me), 1.92-1.78 (2H, m, —CH2—) ppm. 31P NMR (121.4 MHz) δ 25.32 ppm. Anal. calcd. for C32H36IO5P: C, 59.8; H, 5.7; P, 4.8. Found: C, 59.8; H, 5.8; P, 4.5%.

Provenance & Evidence