(Diethoxyphosphinyl)acetic acid → 5-(4-Dimethylamino-phenyl)-penta-2,4-dienoic acid

온도

-65 °C

Butyllithium (24 mL of 2.5 N solution) was added to 120 mL of anhydrous tetrahydrofuran (THF) at −65° C. A solution of diethylphosphonoacetic acid (5.5 g) in 45 mL of anhydrous THF was added dropwise to the stirred solution at −65° C. over a period of one hour. The resulting solution was stirred at −65° C. for an additional 30 minutes and then a solution of p-dimethylaminocinnamaldehyde (5.0 g) in 80 mL of anhydrous THF was added to the reaction at −65° C. over a period of 30 minutes. The reaction was stirred for one hour, allowed to warm to room temperature and then stirred overnight. The reaction was then quenched with 400 mL of water and extracted with 300 mL of ethyl acetate three times. The aqueous layer was acidified with 5% hydrochloric acid (11 mL) to a pH of 6.1. The solid formed was filtered, washed with 75 mL of water and dried to yield 3.83 g of the desired 5-(p-dimethylaminophenyl)-2,4-pentadienoic acid. 1H NMR (DMSO-d6, 300 MHz), δ(ppm) 7.34 (m, 3H), 6.82 (m, 2H), 6.70 (d, 2H), 5.84 (d, 1H), 2.94 (s, 6H).

1. stirringThe reaction was stirred for one hour
2. temperatureto warm to room temperature
3. stirringstirred overnight
4. customThe reaction was then quenched with 400 mL of water
5. extractionextracted with 300 mL of ethyl acetate three times
6. customThe solid formed
7. filtrationwas filtered
8. washwashed with 75 mL of water
9. customdried

ORD 기록

ord-26890e4cd40042b0a589c67af51fe605

출처 데이터셋

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08026280B2