Dichloromethane → HCID 18798690, compound

Participants

Reaction Steps

The title compound was prepared using 7.0 g (29 mmol) of 2-{5-tert-butyl-4-[2-tert-butyl-4-(2-hydroxy-ethoxy)-5-methyl-phenyldisulfanyl]-2-methyl-phenoxy}ethanol (prepared in Example MMM), 200 mL of CH2Cl2, 15.2 g (118 mmol) of diisopropylethylamine and 9.45 g (118 mmol) of chloromethyl methyl ether. The reagents were mixed at 0° C. and stirred at that temperature for 1 hour. The reaction mixture was warmed to room temperature and stirred for 15 hours, then diluted with EtOAc and quenched with 1N HCl. The organic layer was washed with sodium bicarbonate solution and brine and dried (MgSO4). The solvents were removed, and the residue was subjected to flash silica gel chromatography, eluting with EtOAc:hexane (5:95, then switching to 1:4).

Provenance & Evidence