Triphenylphosphine → [6-(2-{3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenoxy}ethyl)(2-pyridyl)]methylamine

Participants

Reaction Steps

To a stirring solution of 3-[1,1-bis(methylethyl)-2-methyl-1-silapropoxy]phenol (200 mg,0.75 mmol),2-[6-(methylamino)-2-pyridyl]ethan-1-ol (104 mg, 0.68 mmol), triphenylphosphine (199 mg, 0.75 mmol) and THF (25 ml), was added diethyl azodicarboxylate (0.12 ml, 0.75 mmol) at 0° C. The reaction was stirred overnight under argon. The solvent was removed under vaccum and the crude product was chromatographed over silica gel to yield 76 mg (28%) of [6-(2-{3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenoxy}ethyl)(2-pyridyl)]methylamine. NMR 1H Cl3CD δ: 7.39 (m, 1H), 7.07 (t, 1H, J=8.0 Hz), 6.5 (m, 3H), 6.25 (d, 1H, J=8 Hz), 4.27 (t, 2H, J=6.8 Hz), 3.06 (t, 2H, J=6.8 Hz), 2.90 (d, 3H, J=8 Hz), 1.28 (m, 3H), 1.10 (d, 18H, J=7.0 Hz).

Provenance & Evidence