1,3-Propanediol → HCID 22946319, compound

Participants

Reaction Steps

To a solution of tetrahydrofuran (100 mL), 1,3-propanediol (1.6 mL, 30 mmol) and phenol 16 (4.3 g, 15 mmol) at 0° C., was added diethyl azodicarboxylate (DEAD, 3.6 mL, 23 mmol) dropwise over 10 min. The solution was warmed to ambient temperature and stirred for 16 h, prior to concentration in vaciio. The oil was partially purified by chromatography on silica gel to provide alcohol 17 (3.9 g) contaminated with Mitsunobu by-products. This material was used directly in subsequent experiments. 1H NMR (300 MHz, CDCl3) δ 6.93 (s, 2H), 6.8 (s, 1H), 5.9 (bs, 1H), 5.18 (d, 2H), 4.4-3.8 (m, 7H), 2.05 (m, 2H), 1.4-1.9 (m, 10H). Mass spectrum (CI) calcd. for C18H24NO3Cl: 338 (M+H). Found: 338.

Provenance & Evidence