Triphenylphosphine → HCID 11392279, compound

Participants

Reaction Steps

3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) in tetrahydrofuran (anhydrous, 10 mL) was treated with 3-phenoxyphenol (Aldrich, 186 mg, 1 mmol), DIAD (diisopropyl azadicarboxylate, Aldrich, 404 mg, 2 mmol), and triphenylphosphine (Aldrich, 522 mg, 2 mmol) at ambient temperature for two days. The reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.30) as oil (250 mg, yield, 85%). 1H NMR (MeOH-d4, 300 MHz) δ 1.42–1.58 (m, 1H), 1.64–1.75 (m, 1H), 1.78–1.88 (m, 1H), 2.00–2.15 (m, 1H), 2.16–2.24 (m, 1H), 2.80–3.1 3.34–3.40 (m, 1H), 4.52 (m, 1H), 6.52 (m, 2H), 6.67(dd, J=2.4, 1.0 Hz, 1H), 6 2H), 7.11 (tt, J=7.5, 1.7 Hz, 1H), 7.23 (t, J=7.8 Hz, 1H), 7.35 (m, 2H) ppm. MS (DCl/NH3) m/z 296 (M+H)+.

Provenance & Evidence