Tetrahydrofuran → Methyl 2-(p-methoxyphenyl)-1-methylthioethyl sulfoxide

Participants

Reaction Steps

1.175 g of methyl methylthiomethyl sulfoxide was dissolved in 5 ml. of tetrahydrofuran, and under cooling with ice, 0.965 g (one equivalent) of sodium hydride was added. The mixture was then stirred for 1 hour. 1.93 g of p-methoxybenzyl bromide (1 equivalent) was added, and the mixture was stirred for 22 hours at room temperature, followed by addition of 40 ml. of methylene chloride and 2 ml. of water. The reaction mixture was dried with sodium sulfate anhydride, and concentrated at reduced pressure. The residue was subjected to column chromatography (silica gel, methylene chloride) to give 1.163 g of methyl 2-(p-methoxyphenyl)-1-methylthioethyl sulfoxide in a conversion yield of 79.1%.

Provenance & Evidence