Methyl iodide → HCID 86590997, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-1-chloro-5-hydroxyhexane, dimethylformamide (100 ml), powdered potassium carbonate (1 g), iodomethane (15.9 g, 112 mmol) and sodium hydride (2.0 g, 84 mmol) were combined was heated at 40° C. for 30 minutes. After cooling to room temperature, water (100 ml) was added cautiously and the mixture was extracted with hexanes (2×100 ml). The combined extracts were concentrated under vacuum and the residue was purified by column chromatography on silica gel eluting with hexanes followed by 10% ethyl acetate-hexanes to afford (R)-1-chloro-5-methoxyhexane (3.1 g, 43% yield for 2 steps) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.15 (d, 3H), 1.36-1.56 (m, 4H), 1.70-1.84 (m, 2H), 3.28 (s, 3H), 3.29 (m, 1H), 3.52 (t, 2H).

Provenance & Evidence