Tetrahydrofuran → HCID 68701713, compound

Participants

Reaction Steps

Cool a solution of Preparation 39 (3.65 g, 12.4 mmol) in THF (90 mL) to −78 C. Add a solution of KHMDS (32 mL, 0.5 M in toluene, 16 mmoL) over 5 min, then allow to stir for 15 in at −78 C. Add hexamethylphosphoramide (HMPA) via syringe (2.8 mL, 16.1 mmoL) quickly, and allow to stir for 20 min at −78 C. Add 2-O-methoxylmethyl allyl iodide (4.24 g) over 2 min, and then allow the solution to warm to −50 C. over 1.5 h. Pour the contents of the reaction into ½ satd. NaHCO3 and extract with Et2O (2×100 mL) and EtOAc (2×100 mL). Wash the combined organic extracts with H2O (2×150 mL) and brine (150 mL) and then dry over Na2SO4. Concentrate the crude product to leave a brown oil, which is purified by MPLC (0% to 12% to 20% EtOAc/hexanes) to afford Preparation 40 (3.72 g, 76%) as a light yellow oil. 1H NMR (CDCl3) δ 7.31-7.44 (m, 5H), 6.98 (d, J=8.8 Hz, 1H), 6.87 (dd, J=8.8, 3.2 Hz, 1H), 6.74 (d, J=3.2 Hz, 1H), 5.66 (m, 1H), 5.01-5.09 (m, 4H), 4.93 (A ob AB, JAB=6.4 Hz, 1H), 4.90 (B of AB, JAB=6.4 Hz, 1H), 4.18 (d, J=2.4 Hz, 1H), 3.87 (d, J=2.4 Hz, 1H), 3.44 (s, 3H), 3.18 (m, 1H), 2.86 (m, 1H), 2.22-2.39 (m, 3H), 2.12 (dd, J=9.4, 14.0 Hz, 1H).

Provenance & Evidence