N-Hydroxyphthalimide → HCID 22946318, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of alcohol 17 (8.8 g, 26 mmol), tetrahydrofuran (100 mL), N-hydroxyphthalimide (3.8 g, 23 mmol) and triphenylphosphine (5.2 g, 20 mmol) was stirred at 0° C. for 5 min. To the mixture was added DEAD (3.4 mL, 20 mmol) dropwise. The reaction mixture was then allowed to warm to ambient temperature and stirred for 12 h prior to concentration in vacuo. The residue was purified by chromatography to provide phthalimide 18 (3.7 g) contaminated with Mitsunobu by-products. This material was used directly in subsequent experiments. 1H NMR (300 MHz, CDCl3) δ 7.78-7.85 (m, 2H), 7.73-7.77 (m, 2H), 6.94 (t, 2H), 6.38 (d, 1H), 5.95 (bs, 1H), 5.18 (d, 2H), 4.40 (t, 2H), 3.8-4.4 (m, 4H), 2.20-2.28 (m, 2H), 1.4-1.9 (m, 1H). Mass spectrum (CI) calcd. for C26H27N2O5Cl: 483 (M+H). Found: 483.

Provenance & Evidence