Benzyl Alcohol → 6-Benzyloxy-1,3-benzoxathiol-2-one

Participants

Reaction Conditions

Reaction Steps

Dissolve 6-hydroxy-1,3-benzoxathiol-2-one (16.8 g, 0.1 mol) in THF (1650 mL) and cool to 0° C. Sequentially add benzyl alcohol (16.2 g, 0.15 mol), triphenylphosphine (PPh3, 39.3 g, 0.15 mol), and diisopropylazodicarboxylate (30.3 g, 0.15 mol). Stir the reaction mixture at room temperature overnight. Add water (1500 mL) and extract the aqueous layer with EtOAc (3×1500 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 10-25% of EtOAc/hexane) to give 24.33 g of 6-benzyloxy-benzo[1,3]oxathiol-2-one (94%).

Provenance & Evidence