Methyl iodide → HCID 19610437, compound

Participants

Reaction Steps

To a solution of Intermediate 2 (0.60 g, 1.88 mmol) in anhydrous DMF (20 ml), at 0° C., was added sodium hydride (0.113 g of a 60% dispersion in oil, 2.81 mmol) and the mixture stirred for 0.2 h, before adding methyl iodide (0.399 g, 2.81 mmol), dropwise. The mixture was warmed to room temperature, stirred for 2 h, and then partitioned between water and ethyl acetate. The organic phase was separated and washed with water (×2) and brine (×1). After drying (MgSO4), the solvent was removed in vacuo and the crude product chromatographed through silica gel eluting with ethyl acetate/hexane (1:1) to give the desired methyl ether (0.365 g, 60%), δ(250 MHz, CDCl3) 1.44 (9H, s, (Me)3), 2.26-2.78 (6H, m, 3 of CH2), 3.02-3.16 (1H, m, CH), 3.31 (3H, s, OMe). 3.34-3.40 (4H, m, 2 of CH2), 3.53-3.69 (2H, m, CH2), 7.19-7.34 (5H, m, Ar-H).

Provenance & Evidence