反应详情

Potassium bis(trimethylsilyl)amide (5.4 g, 0.027 mol) was added to a solution of 18-Crown-6 (13.7 g, 0.052 mol) and (diphenoxy-phosphoryl)-acetic acid tert-butyl ester (9.4 g, 0.027 mol) in dry THF (120 mL) at −780C. After 30 minutes of stirring at this temperature, benzo[b]thiophene-2-carbaldehyde (4.0 g, 0.024 mol) was added and the reaction was stirred for 3 hours at −780C after which the reaction was quenched with saturated ammonium chloride (200 mL). The reaction mix was allowed to come to room temperature and was extracted with ethyl acetate (3×200 mL) and the combined organic extracts were washed with 10% HCl (200 mL), brine (200 mL), and dried over MgSO4. The solvent was evaporated in vacuo leaving the crude product that was purified by column chromatography (SiO2) using a 5-40% ethylacetate-hexane gradient to afford the subtitle compound (4.64 g, yield: 74%). MS calculated for C15H16O2S+H: 261, observed: 261.

1. additionwas added
2. customwas quenched with saturated ammonium chloride (200 mL)
3. additionThe reaction mix
4. customto come to room temperature
5. extractionwas extracted with ethyl acetate (3×200 mL)
6. washthe combined organic extracts were washed with 10% HCl (200 mL), brine (200 mL)
7. dry with materialdried over MgSO4
8. customThe solvent was evaporated in vacuo
9. customleaving the crude product that
10. customwas purified by column chromatography (SiO2)