Triethylamine → (E)-tert-Butyl 2-(2-methoxyethoxymethyl)-3-(4-bromobenzenesulphonyl)acrylate

To a solution of 4-bromobenzenesulphonyl iodide (1.06 g, 3.15 mmol) in dichloromethane (4.5 mL) at room temperature was added tert-butyl 2-(2-methoxyethoxymethyl)acrylate (0.45 g, 2.1 mmol). The mixture was stirred at room temperature for 2.5 hours, cooled to 0° C. and triethylamine (0.58 mL, 4.2 mmol) added dropwise. The reaction was stirred at 0° C. for 0.5 hours and at room temperature for 1.0 hour, diluted with distilled water (20 mL) and dichloromethane (15 mL) and the layers separated. The aqueous layer was further extracted with dichloromethane (2×5 mL) and the combined organic extracts were washed with 1.0M aqueous hydrochloric acid solution (20 mL), 5% aqueous sodium thiosulphate solution (20 mL) and distilled water (20 mL). The dichloromethane phase was dried (MgSO4), filtered and concentrated under reduced pressure to give a brown oil (0.88 g). The crude product was purified by chromatography on silica by gradient elution with hexane/ethyl acetate mixtures to give, after combination and evaporation of appropriate fractions, the title compound as a yellow oil (0.75 g, 83%), Rf =0.39 (silica; hexane/ethyl acetate, 2:1).

1. temperaturecooled to 0° C.
2. stirringThe reaction was stirred at 0° C. for 0.5 hours and at room temperature for 1.0 hour
3. customthe layers separated
4. extractionThe aqueous layer was further extracted with dichloromethane (2×5 mL)
5. washthe combined organic extracts were washed with 1.0M aqueous hydrochloric acid solution (20 mL), 5% aqueous sodium thiosulphate solution (20 mL)
6. distillationdistilled water (20 mL)
7. dry with materialThe dichloromethane phase was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORDレコード

ord-77f0526f8f444a99be55518998191b3f

出典データセット

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05618970