Diethyl Ether → HCID 19843669, compound

Participants

Reaction Steps

Tosyl chloride (3.6 g, 18.9 mmol) is added in portions to a solution of the above diol (4.2 g, 18.9 mmol) in 15 ml of pyridine at 0°-5°. The mixture is stirred at 0° for 1 hour, then is stirred at RT for 1 hour. The reaction is quenched with water; extracted with ether; washed with 2N H2SO4, water, saturated NaHCO3 and brine; and dried. The resulting tosylate (5.8 g, 17.4 mmol) is mixed with sodium hydroxide (0.69 g, 17.4 mmol), ether (20 ml) and water (25 ml), and to this mixture is added 3 drops of tricaprylylmethylammonium chloride (Aliquat 336, Aldrich). The mixture is stirred at RT for 4 hours, then extracted with ether, washed with brine and dried to give 2-(6-methoxyhexylthiomethyl)oxirane.

Provenance & Evidence