1: 78 percent / sodium methoxide / methanol / 16 h / Heating 2: iodine monochloride, sodium azide / dimethylformamide / 1 h / Ambient temperature 3: DAMP, pyridine 4: 1.) m-chloroperbenzoic acid, water, 2.) sodium methoxide / 1.) dichloromethane, RT, 3.5 h, 2.) methanol, RT, 30 min View Scheme

1: 78 percent / sodium methoxide / methanol / 16 h / Heating 2: 50 percent / imidazole / dimethylformamide / 1.25 h / Ambient temperature 3: 4 percent / sodium bicarbonate, m-chloroperbenzoic acid / 0.5 h / Ambient temperature 4: 52 percent / cesium fluoride / dimethylformamide / 3 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103233', constants.ctx, '0')">pyridine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102551', constants.ctx, '0')">1,4-dioxane</a> <br />7&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;