Phthalimide → HCID 69332185, compound

Participants

Reaction Steps

To a stirred solution of 1-benzyloxy-2-(R)-hydroxy-5-hexene (2.18 g, 10.5 mmol), triphenylphosphine (3.32 g, 12.7 mmol) and phthalimide (1.86 g, 12.7 mmol) was added diisopropyl azodicarboxylate (2.62 ml, 12.7 mmol) at rt, and the resulting mixture was stirred for overnight at rt. The mixture was concentrated in vacuo and extracted with EtOAc. The organic layer was washed with water, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent to give 1-benzyloxy-2-(S)-phthalimido-5-hexene (2.95 g, 83%) as a colorless oil: 1H-NMR (CDCl3) δ 1.76–1.84 (m, 2 H), 2.06 (dd, J=14.4, 6.8 Hz), 2 H, 2.12–2.22 (m, 1 H), 3.69 (dd, J=10.0, 5.6 Hz, 1 H), 4.00 (t, J=9.6 Hz, 1 H), 4.46 (d, J=12.0 Hz, 1 H), 4.53 (d, J=12.0 Hz, 1 H), 4.51–4.58 (m, 1 H), 4.91–4.99 (series of m, 2 H), 5.72–5.79 (m, 1 H)7.21–7.26 (m, 5 H), 7.71–7.83 (series of m, 2 H); MS (ESI) m/z, 336 (M++H).

Provenance & Evidence