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

To a solution of 4-chlorobenzenesulphonyl iodide (4.95 g, 16.4 mmol) in dichloromethane (12 mL) at room temperature was added tert-butyl 2-(2-methoxyethoxymethyl)acrylate (2.36 g, 10.9 mmol). The mixture was stirred at room temperature for 23 hours, cooled to 0° C. and triethylamine (2.9 mL, 21.8 mmol) added dropwise. The reaction was stirred at 0° C. for 1.25 hours, diluted with distilled water (25 mL) and dichloromethane (12 mL) and the layers separated. The aqueous layer was further extracted with dichloromethane (10 mL) and the combined organic extracts were washed with 1.0M aqueous hydrochloric acid solution (25 mL), 5% aqueous sodium thiosulphate solution (25 mL) and distilled water (10 mL). The dichloromethane phase was concentrated under reduced pressure to give a brown oil (4.46 g). The crude product was purifed by chromatography on silica by eluting with hexane/ethyl acetate (3:1) to give, after combination and evaporation of appropriate fractions, the title compound as a oil, (3.50 g, 82%), Rf =0.38 (silica, hexane/ethyl acetate, 2:1).

1. temperaturecooled to 0° C.
2. stirringThe reaction was stirred at 0° C. for 1.25 hours
3. customthe layers separated
4. extractionThe aqueous layer was further extracted with dichloromethane (10 mL)
5. washthe combined organic extracts were washed with 1.0M aqueous hydrochloric acid solution (25 mL), 5% aqueous sodium thiosulphate solution (25 mL)
6. distillationdistilled water (10 mL)
7. concentrationThe dichloromethane phase was concentrated under reduced pressure

ORD record

ord-5c41b33931f54496b16224c24ad0aa0c

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05618970