Ammonium Chloride → Ethyl 5-(2,4-dimethoxyphenyl)-2,4-pentadienoate

Temperature

0 °C

To 9.00 g (72.2 mmol) of 50% potassium butoxide, 200 ml of anhydrous tetrahydrofuran was added in the atmosphere of argon. To the mixture, cooled to 0° C., was added dropwise a solution of 25.81 g (72.2 mmol) of triethyl-4-phosphocrotonate dissolved in 30 ml of anhydrous tetrahydrofuran through a dropping funnel over 30 minutes. After 30 min., a solution of 10 g (60.2 mmol) of 2,4-dimethoxybenzaldehyde dissolved in 30 ml of anhydrous tetrahydrofuran was added dropwise through a dropping funnel over 10 minutes. Temperature of the reaction mixture was raised from 0° C. to room temperature followed by stirring for 18 hours. To the resulting mixture were successively added saturated aqueous solution of ammonium chloride and water followed by extraction with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of ammonium chloride, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a residue. It was subjected to column chromatography on silica, and from the ethyl acetate-hexane (1:7) eluate fraction was produced 9.44 g (36.0 mmol) of ethyl 5-(2,4-dimethoxyphenyl)-2,4-pentadienoate.

1. additionwas added dropwise through a dropping funnel over 10 minutes
2. temperatureTemperature of the reaction mixture was raised from 0° C. to room temperature
3. extractionfollowed by extraction with ethyl acetate
4. washThe organic layer was washed with water and saturated aqueous solution of ammonium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto obtain a residue

ORD record

ord-7381feef279f4e41bcd69be1493d3904

Source dataset

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04792553