反应详情

To an efficiently stirred solution of triphenylphosphine (81 g, 309 mmol) in THF (200 mL) was added diethyl azodicarboxylate (62.5 g, 309 mmol) at 0° C. The mixture was stirred for 30 min, after which time a thick white precipitate was obtained. The crude 4-(tert-butydimethylsilyloxy)-benzyl alcohol (48 g) in THF (100 mL) and thiolacetic acid (36.1 g, 474 mmol) were added dropwise while the temperature was maintained below 10° C. The reaction was stirred overnight while keeping the internal temperature below 10° C. The solvent was removed in vacuo and the residue was purified by flash column chromatography [SiO2: isohexane-ethyl acetate (9:1)] to give the product as a viscous brown oil (30.7 g, 50%).

1. customafter which time a thick white precipitate was obtained
2. temperaturewas maintained below 10° C
3. stirringThe reaction was stirred overnight
4. customthe internal temperature below 10° C
5. customThe solvent was removed in vacuo
6. customthe residue was purified by flash column chromatography [SiO2: isohexane-ethyl acetate (9:1)]