Chloroiodomethane → Benzyl chloromethyl pentanedioate

Participants

Reaction Steps

A mixture of 1.5 g (3.75 mmole) tetrabutylammonium benzyl glutarate and 20 ml chloroiodomethane is stirred at room temperature for three hours and concentrated in vacuo to a viscous oil. The oil is taken up in 20 ml ethyl acetate and 30 ml hexane and filtered to remove tetrabutylammonium iodide. The solvent is evaporated in vacuo and the residue purified by chromatography on 75 g silica gel, eluting with 70:30 ethyl acetate/hexane by volume. Fractions (15 ml) were collected every 0.7 minutes. The fractions containing the desired product (fractions 8-11) are combined and the solvent evaporated in vacuo to yield 0.55 g (62.5%) of the desired product. 1H-NMR (CDCl3) ppm (delta): 1.65-2.2 (m, 2H), 2.26-2.64 (m, 4H), 5.1 (s, 2H), 5.65 (s, 2H), 7.3 (s, 5H).

Provenance & Evidence