Diethyl Ether → HCID 68704484, compound

Participants

Reaction Steps

To a 0 C solution of Preparation 27 (10.0 g, 30.8 mmol) in THF (125 mL) add a solution of allyl magnesium chloride in Et2O (46 mL, 1.0 M, 46 mmol). Maintain the reaction at 0 C for 30 min, then pour the reaction contents into a solution of ½ satd. NaHCO3 (250 mL). Extract the solution with Et2O (2×150 mL) and EtOAc (150 mL). Wash the combined organic extracts with H2O (150 mL) and brine (150 mL), dry the organics over Na2SO4, and concentrate to afford a brown oil. Purify the product by MPLC (0% to 15% to 25% EtOAc/hexanes) to afford Preparation 38 (7.72 g, 68%) as a light yellow solid. 1H NMR (CDCl3) δ 7.31-7.43 (m, 5H), 7.01 (d, J=8.8 Hz, 1H), 6.87 (dd, J=8.8, 3.0 Hz, 1H), 6.79 (d, J=3.0 Hz, 1H), 5.71 (m, 1H), 5.15 (dd, J=0.8, 9.8 Hz, 1H), 5.10 (dd, J=0.8, 17.6 Hz, 1H), 5.04 (A of AB, JAB=14.2 Hz, 1H), 5.03 (B of AB, JAB=14.2 Hz, 1H), 4.08 (m, 2H), 3.80 (d, J=2.4 Hz, 1H), 3.41 (m, 1H), 2.35 (m, 2H), 1.08 (t, J=7.2 Hz, 3H).

Provenance & Evidence